Category: 675109-26-9

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 675109-26-9, name is 6-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 6-Bromoisoindolin-1-one

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10% acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80%). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J- 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

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

Reference of 675109-26-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 675109-26-9, name is 6-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a degassed solution of 6-bromoisoindolin-1-one (0.7 g, 3.3 mmol), 1-Boc pperazine (0.921 g, 4.9 mmol) and sodium tert butoxide (0.95 g, 2.5 mmol) in toluene (10 mL),Pd2(dba)3 (0.151 g, 0.l6Smmol) and BINAP (0.205 g, 0.33 mmol) were added at rt and heated to 80 C overnight in sealed tube. Then the reaction mixture was filtered through celite and concentrated. Water (4 mL) was added and was extracted with EtOAc (2 x 10 mL). The combined organic layer was dried over Na2SO4 and concentrated under vacuum. The resulting crude product was purified by flash chromatography (Eluent: 5-6% MeOH inDCM). After evaporation, the resulting solid was triturated in Et20 and filtered, affording the title product (white solid). 1H NMR (400 MHz, CDCI3): 6 8.72-8.70 (m, IH), 7.79 (d, J = 1.6 Hz, IH), 7.56 (d, J = 8.4 Hz, IH), 7.26-7.23 (m, IH), 4.26 (5, 2H), 3.49-3.46 (m, 4H), 3.18- 3.13 (m, 4H), 1.43 (5, 9H). LCMS: (Method A) 318.0 (M+H), Rt. 2.26 mm, 39.9% (Max).

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.

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

(4) The compound obtained in step (3) (80 g, 0.38 mol) was dissolved in 1 L of dichloromethane.A 1 N solution of borane tetrahydrofuran (1 L) was added dropwise and stirred at room temperature for 4 hours.Then heated to reflux for 3 hours. The system cooled down,100 ml of 2N hydrochloric acid was added dropwise and the mixture was stirred at room temperature for 3 hours and then refluxed for 4 hours. Cooling filtration,The cake was washed with dichloromethane to give an off-white powder that was the target.

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

Reference:
Patent; Shanghai Xinyuan Pharmaceutical Technology Co., Ltd.; Wu Tianjun; (9 pag.)CN107474006; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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 63: 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-isoindol-1 – one (1578) (1579) A stirred mixture of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (780 mg, 3.68 mmol), (1580) bis(pinacolato)diboron (1.089 g, 4.28 mmol) and potassium acetate (1.26 g, 12.87 mmol) anhydrous 1 ,4-dioxane (12 mL) was degassed with nitrogen for 5 minutes. 1 ,1′- bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (150 mg, 0.18 mmol) was then added and the reaction heated under nitrogen at 100C for 16 hours. After cooling to room temperature the mixture was diluted with water and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under vacuum to yield the title compound (1.1 g, 115 %) which was used crude without purification. MS: [M+H]+ = 260.

Statistics shows that 6-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 675109-26-9.

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

Synthetic Route of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Pd2(dba)3 (350 mg, 0.38 mmol), XantPhos (540 mg, 0.93 mmol), cesium carbonate (9 g, 27.8 mmol, 2 eq), 6-bromo-isoindolin-1-one (XVII) (2.94 g, 14 mmol, 1 eq) and methyl 6-bromopicolinate (X) (3 g, 14 mmol, 1 eq) were combined in dioxane (100 mL). The mixture was degassed with nitrogen, sealed and heated at 80 C. for overnight. The reaction mixture was poured into water (100 mL). A precipitate formed was filtered and the filtrate was extracted with EtOAc (3*50 mL). The organic extracts were combined and concentrated. The resulting solid was triturated in IPA to give methyl 6-(6-bromo-1-oxoisoindolin-2-yl)picolinate (XVIII) as a solid (3.5 g, 73% yield). 1HNMR (400 MHz, DMSO-d6) delta 3.90 (s, 3H), 5.12 (m, 2H), 7.73 (m, 1H), 7.85 (m, 1H), 7.95 (m, 2H), 8.10 (m, 1H), 8.70 (m, 1H).

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

Reference:
Patent; Hepatikos Therapeutics, LLC; Smith, Christopher Ronald; Chapman, Justin; US2020/2312; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9, A common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

6-Bromoisoindolin-1-one (636 mg, 3.10 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (930 mg, 3.70 mmol), and Pd(dppf)Cl2 (125 mg, 0.150 mmol) were added to a dry flask and placed under N2. Potassium acetate (900 mg, 9.20 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (DMF) (18 mL) was added and the reaction was heated at 80 C. overnight. The reaction mixture was evaporated to dryness and the resulting material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (493 mg, 62%). ESI-MS m/z calc. 259.1, found 260.1 (M+1)+. Retention time 1.24 minutes.

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; HADIDA RUAH, SARA S.; Miller, Mark; Zhou, Jinglan; Bear, Brian; Grootenhuis, Peter; US2009/143381; (2009); 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.

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]+.

Statistics shows that 6-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 675109-26-9.

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

Electric Literature of 675109-26-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 675109-26-9, name is 6-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

[0420] To a solution of Example 59a (317 mg, 1.5 mmol), Example 59b (470 mg, 1.5 mmol), K3P04 (636 mg, 3 mmol), Cul (29 mg, 0.15 mmol) in dioxane (7 mL) was added N1,N2-dimethylcyclohexane- 1,2-diamine (43 mg, 0.3 mmol). Then mixture was degassed with N2 three times and sealed, which was stirred at 100C for 30 min under microwave. The mixture was diluted with water (100 mL) and extracted with DCM (100 mL*l, 50 mL*2) The combined DCM layer was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH = 100/0 to 94/6) to give the desired productExample 59c (400 mg, yield 67%) as a pale yellow solid. LCMS [M+l]+ = 397.9

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Combine 6-bromo-2, 3-dihydro-isoindol-1-one (0.200 g, 0.94 mmol), bis- pinocalatodiboron (0.264 g, 1.04 mmol), palladium (II) acetate (16 mg, 0.07 mmol) and tricyclohexylphosphine (26 mg, 0.09 mmol) in a 50 mL flask. Add acetonitrile (10 mL) and cesium fluoride (0.428 g, 2.82 mmol); fit flask with condenser and heat in a 90 C oil bath for 1 hour. Cool to room temperature and add trifluoro-methanesulfonic acid 6- methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (0.200 mg, 0.38 mmol), palladium (II) acetate (13 mg, 0.05 mmol) and tricyclohexylphosphine (20 mg, 0.07 mmol), cesium fluoride (0.172 g, 1.13 mmol) and acetonitrile (5 mL). Heat mixture in a 90 C oil bath for 1 hour. Cool reaction to room temperature and filter through celite and wash celite pad with ethyl acetate (60 mL). Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting the material with methanol in dichloromethane (0 to 15%) to give 110 mg of the title compound (57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

6-Bromoisoindolin-l-one (CAS 675109-26-9) (1.61 g, 7.58 mmol, 1.05 equiv.) was suspended in 32 ml of THF and cooled to 0-5C. Sodium hydride (60% dispersion in mineral oil) (318 mg, 7.94 mmol, 1.1 equiv.) was added at 0-5C. The reaction mixture was stirred at room temperature for 15 minutes and then cooled to 0-5C. Methyl (2RS)-2-bromo-2-(5-fluoro-2- methoxyphenyl)acetate (CAS 1368458-30-3) (2.00 g, 7.22 mmol) dissolved in 8.0 ml of THF was added dropwise at 0-5C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4CI- solution and extracted with ethyl acetate. The aqueous layer was backextracted with ethyl acetate. The organic layers were washed with water and brine. The organic layers were combined, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane 0: 100 to 50:0 gradient to obtain the desired methyl (2RS)-2-(6-bromo-l-oxo- isoindolin-2-yl)-2-(5-fluoro-2-methoxy-phenyl)acetate (2.202 g, 75 % yield) as a yellow foam, MS: m/e = 408.0/410.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; JAESCHKE, Georg; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; DUPLESSIS, Martin; NAGEL, Yvonne Alice; KUHN, Bernd; (60 pag.)WO2018/220149; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem