Category: 675109-26-9

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 675109-26-9 as follows. Recommanded Product: 675109-26-9

A stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (3.4 g, 14.16 mmol) and 2-chloro-1- (1 ,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one (3.6 g, 17.00 mmol) in DMF (47 mL) was cooled in an ice bath under nitrogen before adding NaH (0.70 g, 17.00 mmol) in portions. The reaction was allowed to warm to room temperature over an hour and was then quenched with NH4CI (sat., aq.). The pH was adjusted to pH 7 with citric acid (5%, aq.) and the product was extracted with IPAiCHCh (1 :3, x3). The combined organic layers were washed brine, dried over MgS04, filtered and concentrated under vacuum to yield 6-bromo-2-[2-oxo-2-(1 ,2,3,4- tetrahydroisoquinolin-2-yl)ethyl]-2,3-dihydro-1 H-isoindol-1 -one as a brown solid which was used crude. MS: [M+H]+ = 385.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 675109-26-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 675109-26-9 name is 6-Bromoisoindolin-1-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 6-bromoisoindolin-1-one (7.00 g, 3.30 mmol) and 1, 4-dioxane (125 mL), were added bis (pinacolato)diboron (17.00g, 6.60mmol), KOAc (8.50 g, 8.25 mmol) and Pd(dppf)Cl2 (2.50 g, 0.33 mmol). The reaction mixture was stirred at 90 oC for 12h under N2 atmosphere. After cooling to r. t. the reaction mixture was filtered. The solvent evaporated under reduced pressure then added ethyl acetate (80 mL). The precipitate was filtered to obtained black solid. Yield 70%, m.p. > 250oC. 1H NMR (300 MHz, CDCl3) delta (ppm): 8.36 (s, 1H, ArH), 8.00 (d, J = 7.60 Hz, 1H, ArH), 7.48 (d, J = 7.60 Hz, 1H, ArH), 7.03 (s, 1H, NH), 4.48 (s, 2H, CH2), 1.35 (s, 12H, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 675109-26-9, COA of Formula: C8H6BrNO

General procedure: To a solution of 6-bromo-2-methylisoindolin-1-one (5 g,22.1 mmol) in dmf (30 mL) was added bis(pinacolato)diboron (6.18 g,24.3 mmol) and potassium acetate (6.51 g,66.4 mmol). The reaction mixture was degassed and backfilled with N2 gas,and 1,1 ?-bis(diphenylphosphino)fenocene palladium(II)dichloride dichloromethane (0.903 g,1.106 mmol) was added.The reaction mixture was stined at 80 C for 10 hours. After diluting with EtOAc and water, The organic layer was concentrated and purified on silica column (100% EtOAc) to get the product as a mixture of the title compound as a boronic ester and boronic acid,which was not further purified.MS: 274 (m+1)?H NMR (500 MHz,CDCl3): oe 8.33 (s,1H),7.98 (d,7.5 Hz,1H),7.46 (d,7.5 Hz,1H),4.41 (s,2H),3.22 (s,3H),1.38 (s,12H). The following intermediates in table c were preparedaccording to scheme c using the procedure outlined in the synthesis intermediate cl using 1,1?-bis(di-tert-butylphosphino)fenocene palladium dichloride or 1,1 ?-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane complex as the palladium catalyst with toluene or dmf as the reaction solvent. The starting material bromide was either commercially available,known in the literature,or prepared using the protocol in scheme B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John J.; BAO, Jianming; EGBERTSON, Melissa; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra Lee; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert D., Jr.; MENG, Zhaoyang; RUDD, Michael T.; SELYUTIN, Oleg; TELLERS, David M.; TONG, Ling; WAI, Jenny Miu-Chun; (125 pag.)WO2017/107089; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromoisoindolin-1-one

To a mixture of 6-bromo-2,3-dihydro-isoindol-1-one (10.0 g), DMAP (11.5 g) and THE (100 mL), (Boc)20 (15.4 g) was added and the mixture was stirred at room temperature for 12 hours. The resulting yellow mixture was partitioned between water and ethyl acetate, and the phases were separated. The organic phase was washed with brine anddried over Na2504. After filtration and evaporation of the solvent, the resulting residue was purified by column chromatography (silica gel, PE/EA = 15:1)to provide the subtitle compound. MS ESl: mlz = 256 [Mi-H-tBu].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BUNING, Christian; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; HALLAND, Nis; LOHMANN, Matthias; POeVERLEIN, Christoph; RITTER, Kurt; WO2015/150565; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 675109-26-9, SDS of cas: 675109-26-9

Preparation 48: 6-bromo-2-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1 H-isoindol-1 -one (1544) (1545) Sodium hydride (60% dispersion in mineral oil, 34 mg, 1.40 mmol) was added to a suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (250 mg, 1.18 mmol) in DMF (5 mL) and the mixture was stirred for 5 min after hydrogen gas evolution ceased. 4-(2-bromoethyl)morpholine (0.18 mL, 1.3 mmol) was added to the resulting brown solution and the mixture was stirred at RT for 18 h. The mixture was diluted with ethyl acetate and transferred into a separating funnel. Water was added and the crude product was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgS04) and concentrated under vacuum. The residue was triturated with a mixture of diethyl ether and iso-hexane and the resulting precipitate was filtered, washed with iso-hexane and dried under suction to afford the title compond (196 mg, 50%) as a pale yellow solid. LC-MS: [M+H]+ = 325/327.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation 124: Methyl 3-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)propanoate (1728) To a stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1-one (550 mg, 2.59 mmol), 18-crown-6 (69 mg, 0.26 mmol) and methyl 3-bromopropionate (350 pL, 3.1 1 mmol) in DMF (9 ml.) was added CS2CO3 (2.113 g, 6.48 mmol) under nitrogen. The reaction was heated to 70 C (1729) (thermally) slowly and maintained at this temperature for 18 hours. After cooling and the reaction was quenched with NH4CI (sat., aq.). The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and (1730) concentrated under vacuum to yield methyl 3-(6-bromo-1-oxo-2,3-dihydro-1 H-isoindol-2- yl)propanoate as a yellow oil. LC-MS was consistent with a complex mixture which was taken on as is. To the residue was added bis(pinacolato)diboron (0.746 g, 2.91 mmol), AcOK (0.491 mg, 5.00 mmol) and anhydrous 1 ,4-dioxane (8 ml_). The reaction was degassed with nitrogen for 5 minutes. 1 ,1 ‘-Bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (61 mg, 0.08 mmol) was then added and the reaction heated at 90C under nitrogen for 16 hours. The reaction was allowed to cool to room temperature and was then diluted with water. The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and concentrated under vacuum to yield the title compound (1.5 g, 168 %) which was used without further purification. MS: [M+H]+ = 346.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

General procedure: Step 1: A glass vial was charged with corresponding bromo-heteroaryl compound (0.20mmol, 1eq), potassium metabisulfite (88mg, 0.40mmol, 2eq), tetrabutylammonium bromide (70mg, 0.22mmol, 1.1eq), sodium formate (15mg, 0.22mmol, 1.1eq), palladium(II) acetate (5mg, 0.02mmol, 0.1eq), triphenylphosphine (16mg, 0.06mmol, 0.3eq), 1,10-phenanthroline (11mg, 0.06mmol, 0.3eq). After sealing, the vial was flushed with argon for 30min and the reagents were suspended in dry, degassed DMSO (1mL) and the reaction mixture was stirred for 4h at 70C. After cooling to RT N,N-Diisopropylethylamine (70muL, 0.40mmol, 2eq) and a solution of tert-butyl (E)-(2-aminoethyl)(3-(4-(pyridin-3-yl)phenyl)allyl)carbamate (63) (106mg, 0.30mmol, 1.5eq) in dry THF (1mL) were added and the reaction mixture was cooled to 0C. Subsequently a solution of N-bromosuccinimide (62mg, 0.40mmol, 2eq) in dry THF (1mL) was added and the reaction mixture was allowed to come to RT. After stirring for 1h the reaction was quenched by adding H2O (1mL) and brine (2mL). The resulting mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the solvent removed under reduced pressure. The residue was purified via flash-column-chromatography (SiO2, 0% to 5% MeOH in DCM) to yield the desired Boc-protected product, which was used directly in step 2.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Grimm, Sebastian H.; Gagestein, Berend; Keijzer, Jordi F.; Liu, Nora; Wijdeven, Ruud H.; Lenselink, Eelke B.; Tuin, Adriaan W.; van den Nieuwendijk, Adrianus M.C.H.; van Westen, Gerard J.P.; van Boeckel, Constant A.A.; Overkleeft, Herman S.; Neefjes, Jacques; van der Stelt, Mario; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 692 – 699;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 675109-26-9, Recommanded Product: 675109-26-9

A mixture of 6-bromoisoindolin-1-one (287 mg, 1.35 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (500 mg, 1.35 mmol), Pd(dppf)Cl2 (33 mg, 0.041 mmol) and Cs2CO3 (1.32 g, 4.05 mmol) in dioxane (50 mL) and water (8 mL) was heated to 100 C. overnight. After cooling, the mixture was concentrated under vacuum and purified by column chromatography on silica gel ((1%-3% MeOH in DCM) to afford 9A (220 mg, 76% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) delta 8.66 (s, 1H), 7.76-7.15 (m, 4H), 7.15 (s, 1H), 4.43 (s, 2H), 3.72 (s, 3H); ESI m/z 214.1 [M+1]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 675109-26-9

[1532] to a solution of 6-bromoisoindolin-1-one (0.5 g, 2.36 mmol) in acetone (20 ml) was added bnbr (605 mg, 3.54 mmol, 0.420 ml),Cs2CO3 (1.92 g, 5.90 mmol) and 18- crown-6 (62 mg, 235.80 umol), then the mixture was stirred at 70 C for 16h. The reaction mixture was concentrated to remove solvent, then diluted with water (50 ml) and extracted with ea (40 ml x 2), and the organic layers were dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by flash silica gel chromatography (isco; 12 g sepaflash silica flash column, eluent of 0-20% ethyl acetate/petroleum ethergradient 30 ml/min). Compound 378a (0.46 g, yield: 59.5%) was obtained as white solid. 1H NMR (400mhz, CDCl3) delta 8.02 (d, j = 1.8 hz, 1h), 7.63 (dd, j = 1.9, 8.0 hz, 1h), 7.39 – 7.16 (m, 6h), 4.79 (s, 2h), 4.21 (s, 2h). MS (ESI) m/z (M+H)+ 302.0.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 675109-26-9 as follows. 675109-26-9

Preparation 42: 6-bromo-2-[(3-methyloxetan-3-yl)methyl]-2,3-dihydro-1 H-isoindol-1 -one (1538) (1539) A stirred suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (300 mg, 1.42 mmol) in DMF (4 mL) was cooled in an ice-bath and treated with sodium hydride (60% dispersion in mineral oil, 68 mg, 1.70 mmol) and stirred and cooled for 15 min. The mixture was treated with 3- (bromomethyl)-3-methyloxetane (280 mg, 1.70 mmol) and stirred at RT for 18 h. Brine (20 mL) was added and the crude product was extracted with ethyl acetate (2x 20 mL). The combined extracts were washed with brine (20 mL), dried (MgS04) and evaporated. The residue was purified by chromatography (S1O2, 20-100% ethyl acetate in /so-hexane) to afford the title compound (342 mg, 81 %) as a yellow solid. LC-MS: [M+H]+ = 296/ 298.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem