Category: 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. name: 6-Bromoisoindolin-1-one

6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (3Og, 0.14mole), bis (triphenylphosphine) palladium dichloride (5 g, 0.007 mole), CuI (2.6 g, 0.01 mole), dry Et3N (700 mL) in dry DMF (700 mL) was added 3-butyn-1-ol (21.3 mL, 0.28 mole) slowly drop- wise. The reaction mixture was bubbled with argon for 20 min and heated at 100 C for 24 h. The solvent was evaporated and the crude residue was washed with DCM (100 mL), filtered and dried to 6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-one as a pale grey solid (24 g, 85%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H1 s), 7.5-7.6 (2H, d), 7.5 (1H,s), 4.9 (1H, t), 4.3 (2H1 s), 3.6-3.7 (2H, t), 2.4-2.6 (2H, t); MS: M+1: 202 (201)

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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.

A mixture of 78 6-bromoisoindolin-1-one (5.0 g, 23.58 mmol), 176 Pd(AcO)2 (528 mg, 2.30 mmol), Xantphos (1.36 g, 2.36 mmol) and 177 TEA (1.19 g, 117.9 mmol) in 170 methanol (100 mL) was heated to 70 C. under 1 atm of 178 CO (gas) overnight. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by silica column chromatography (1%-2% 23 MeOH in 31 DCM) to give 72A (500 mg, 11% yield) as a white 179 solid: ESI m/z 192.1 [M+H]+ .

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; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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 1 : ferf-Butyl 2-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)acetate (1439) (1440) A suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (20 g, 94 mmol) and tert-butyl 2- bromoacetate (16.94 ml, 1 13 mmol) in DMF (320 mL) was cooled in an ice bath. Sodium hydride (4.53 g, 113 mmol) was added cautiously portionwise and the reaction was allowed to slowly warm to room temperature for 3 h. The reaction was quenched by the addition a saturated solution of NhUCI (650 mL) and the crude product was extracted with DCM (2 x 650 mL). The combined organic extracts were washed with water (4 x 650 mL) and brine (2 x 650 mL). The mixture was passed through a phase separator cartridge and the organic phase was concentrated under vacuum to give the crude product (40.1 g) as a dark orange semi-solid. 30g of the crude product were purified by chromatography (Si02, 2 x 220 g column, 0-50% EtOAc in isohexane) to afford the title compound as a yellow solid (19.5 g, 77%). LC-MS: [M-tBu+H]+ = 270/272.

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., Safety of 6-Bromoisoindolin-1-one

6-(5-Hydroxy-pent-1 -ynyl)-2,3-dihydro-isoindolin-1 -oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (40 g, 0.18 mol), bis(triphenylphosphine) palladium dichloride (6.6 g, 0.009 mol), CuI (3.57 g, 0.01 mol) and Et3N 5 (930 mL) in dry DMF (930 mL) was slowly added 4-pentyn-1-ol (33.2 mL, 0.37 mol). The reaction mixture was bubbled with argon for 20 min and heated at 100 “C for 24 h. The solvent in the reaction mixture was evaporated and the crude residue was washed with DCM(100 mL), filtered and dried to give e-^-Hydroxy-pent-i-ynyl^.S-dihydro-isoindolin-i-one as a black solid (25 g, 61%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H, s), 7.5-7.6 (2H, d), 7.5 0 (1H, S), 4.5 (1H, t), 4.3 (2H, s), 3.5 (2H, s), 2.4-2.5 (2H, s), 1.6 (2H, q); MS: AP: M+1: 216(215).

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; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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, Quality Control of 6-Bromoisoindolin-1-one

A mixture of 6-bromoisoindolin-i-one (5 g, 23.6 mmol), sodium azide (3.07 g, 47.2 mmol), sodium ascorbate (234 mg, 1.18 mmol), Cul (450 mg, 2.36 mmol) and trans-N,N-dimethyl- 1 ,2-diaminocyclohexane (504 mg, 3.54 mmol) in ethanol (35 mE) and water (15 mE) was stirred at reflux for 5.5 h under nitrogen. The reaction mixture was allowed to cool to room temperature and extracted with EtOAc (100 mEx3). The combined organic fractions were washed with brine and dried with anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel (10- 50% EtOAc in pet. ether) to give iSA (1.2 g, 29% yield) as an off-white solid. ESI mlz 175.0 [M+i].

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

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. HPLC of Formula: C8H6BrNO

TDI01239-1 (500 mg, 2.358 mmol) was dissolved in tetrahydrofuran (24 mL), and cooled to 0 C. Under theprotection of nitrogen, 60% NaH (236 mg, 5.895 mmol) was added to the above reaction solution, and the reaction wasperformed at room temperature for 1h after the addition. Bromoethyl acetate was then added at 0 C, and the reactionwas continued at room temperature for 2h. LC-MS indicated the reaction was complete. After completion of the reaction,ice water and IN HCl solution was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate(15 mL). The combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate andconcentrated to dryness to afford TDI01239-2 (700 mg, yellow solid, yield: 99.57%). MS m/z (ESI): 298.1 [M+H].

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); 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.

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

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:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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. SDS of cas: 675109-26-9

6-Bromoisoindolin-l-one (4 g, 18.9 mmol) was suspended in 70 ml of THF and cooled to 0-5C. Sodium hydride (60% in mineral oil) (1.5 g, 37.7 mmol, 2 equiv.) was added in portions at 0-5C and after 5 minutes (2RS)-2-bromo-2-phenyl-acetic acid (4.34 g, 20.2 mmol, 1.07 equiv.) were added and the mixture was stirred at 0-5 C for 2 hours. The reaction mixture was extracted with 1M HC1 solution and twice with ethyl acetate. The organic layers were dried over sodium sulfate and evaporated to dryness to obtain the desired (2RS)-2-(6-bromo-l-oxo-isoindolin-2-yl)-2- phenyl-acetic acid (5.78 g, 89 % yield) as a white solid, MS: m/e = 345.9/347.9 (M+H+).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; DUPLESSIS, Martin; JAESCHKE, Georg; KUHN, Bernd; LAZARSKI, Kiel; LIANG, Yanke; NAGEL, Yvonne Alice; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; (46 pag.)WO2019/149922; (2019); 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.

Example 265: (S)-3-Oxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)- pyridin-2-yl)methyl)isoindoline-5-carboxamide To a 25 mL round bottom flask containing (S)-(4-(trifluoromethyl)- phenyl)(3 -(trifiuoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (120 mg, 0.336 mmol) was added toluene (3 mL). The resulting mixture was stirred at rt for 2 min. At this time,sodium carbonate (143 mg, 1.346 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (3.89 mg, 6.73 muiotaetaomicron), palladium (II) acetate (1.5 mg, 6.7 muiotaetaomicron) and 6-bromo-2,3-dihydro-isoindol-l-one (71.3 mg, 0.336 mmol) were added to the flask. The reaction vessel was flushed with argon and then left under 1.0 atm of carbon monoxide gas (from a lecture bottle, in hood). The flask was heated to 85 C overnight, filtered though Celite brnad filter agent, and eluted with EtOAc. Purification by reverse phase HPLC, and concentration of the containing fractions gave (S)-3-oxo-N-((4-(trifiuoromethyl)- phenyl)(3-(trifiuoromethyl)pyridin-2-yl)methyl)isoindoline-5-carboxamide as a yellow foamy solid. 1H NMR (300MHz , CDC13): delta ppm 8.92 (d, J = 4.5 Hz, 1H), 8.40 (d, J = 7.7 Hz, 1 H), 7.60 – 7.56 (m, 5 H), 7.46 – 7.48 (m, 2 H), 6.90 (d, J = 7.6 Hz, 1 H), 4.54 (s, 2 H). MS 480.1 (M+H).

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 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.

Preparation 314: Mixture of 6-bromo-2-(2-methoxyethyl)isoindolin-1-one and 6-bromo- 2,3-bis(2-methoxyethyl)isoindolin-1 -one (2064) (2065) Sodium hydride (60% wt in mineral oil) (0.1 13 g, 2.83 mmol) was added to a stirred solution of 6-bromoisoindolin-1-one (0.5 g, 2.358 mmol) and 1-bromo-2-methoxyethane (0.277 ml, 2.83 mmol) in DMF (12 mL) under nitrogen at 0 C. The resulting orange solution was allowed to warm slowly to room temperature and stirred for 3 days. The reaction was quenched with water (15 mL) and extracted with EtOAc (3 x 15 mL). The organic extracts were combined and washed with brine (50 mL), dried (MgS04), filtered, and concentrated in vacuo to afford a yellow oil. The crude product was purified by chromatography (S1O2, 24 g GRACE column, 0-100% EtOAc in isohexane) to afford a mixture of 6-bromo-2-(2-methoxyethyl)isoindolin-1-one (549 mg, 62.9%) and 6-bromo-2,3-bis(2-methoxyethyl)isoindolin-1-one as a yellow oil (~3: 1 ratio by LCMS and NMR analyses). Further purification by chromatography (S1O2, 24 g GRACE column, 0-10% MeOH in DCM) did not improve ratio of products, which was used without further purification in the next step. LCMS: [M+H]+ = 270 and 328.

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.