Category: 923590-95-8

Reference of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

Adding a sodium hydroxide solution to the solution containing Compound I, And extracted with dichloromethane, Add Boc 2 O dropwise, react overnight, add water, separate dichloromethane, wash twice with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, separate and purify by column chromatography, use 100-200 mesh silica gel column, wash Deionization using PE (petroleum ether): EA (ethyl acetate) = 40:1-20:1, to give an off-white solid 45g.

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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 solution of 4-bromoisoindoline hydrochloride (8.00 g, 34.33 mmol) in dichloromethane (20 mL) and triethylamine (14.3 mL, 103.0 mmol) was cooled to 0 C, and then di-tert-butyl dicarbonate (15.0 g, 68.73 mmol) was added. The mixture stirred overnight at room temperature and was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of dichloromethane, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 :5)) to afford tert-butyl 4-bromoisoindoline-2-carboxylate (9 g, 75%) as a white solid. MS: (ESI, m/z): 242 [M-t-Bu+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindoline hydrochloride, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 923590-95-8, name is 4-Bromoisoindoline hydrochloride, 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 923590-95-8, SDS of cas: 923590-95-8

Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 chi 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75%). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).

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, 4-Bromoisoindoline hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 923590-95-8

A solution of 4-bromoisoindoline hydrochloride (8.00 g, 34.33 mmol) in dichloromethane (20 mL) and triethylamine (14.3 mL, 103.0 mmol) was cooled to 0 C, and then di-tert-butyl dicarbonate (15.0 g, 68.73 mmol) was added. The mixture stirred overnight at room temperature and was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of dichloromethane, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 :5)) to afford tert-butyl 4-bromoisoindoline-2-carboxylate (9 g, 75%) as a white solid. MS: (ESI, m/z): 242 [M-t-Bu+H]+

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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. SDS of cas: 923590-95-8

Step 4: 1-t-Butyl 2-methyl (2S,4R)-4-(11(4-bromo-1,3-dthydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboicylate To a solution of (2S,4R)-B0C-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+14)* ; calcd for C20H20BrN2O6: 471.1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 923590-95-8, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; US2010/160403; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

General procedure: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

923590-95-8, name is 4-Bromoisoindoline hydrochloride, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Bromoisoindoline hydrochloride

To a solution of (2S,4R)-BOC-4-hydroxyproline methyl ester (126.3 g,515 mmol) in DMF (960 mL) at 00C was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at RT for 3 hours. 4-Bromoisoindoline hydrochloride (12O g, 515 mmol) and DIPEA (96.3 mL, 540 mmol) were added, and the reaction mixture heated to 50C for 6 hours. The reaction mixture was then allowed to cool to RT and stirred overnight. The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+H)+; calcd for C20H26BrN2O6: 471.1].

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 923590-95-8, 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 923590-95-8 as follows.

General procedure: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

According to the analysis of related databases, 923590-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); 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 923590-95-8 as follows. Application In Synthesis of 4-Bromoisoindoline hydrochloride

3. Kumada Coupling of Bromo-Iso-Indole [0258] bromoisoindoline HCl salt (25 g, 106.6 mmol), Pd(OAc)2 (0.199 g, 0.533 mmol), and the ligand (di-tert-butylneopentylphosphonium tetrafluoroborate, 0.325 g, 1.066 mmol). PhMe (toluene) (450 mL, de-oxygenated via sparging with N2) was then added, and the resulting slurry was then cooled to Ti=5 C. using an external bath. Allylmagnesium chloride (1.7 N in THF, 207 mL, 351.8 mmol) was charged to an addition funnel via cannula, and then added at a rate such that Ti<20 C. The resulting solution was then was heated to Ti=45-50 C. [0260] After 16 hours, LC showed >99% conversion of starting material. The reaction was cooled to room temperature, and then was inverse-quenched into 250 mL of 15% aqueous citric acid. The phases were separated, and the aqueous phase containing the product was held while the dark organic phase was rejected. The extractor that contained the aqueous phase was charged with 125 mL of PhMe. The pH of the aqueous phase was adjusted by the addition of 115 mL of NH4OH. The phases were separated, and the organic phase containing the product was held while the aqueous phase was rejected. The organic phase was washed with 20 mL of 15% aqueous NaCl. The PhMe solution was concentrated with azeotrope to a 10 volume solution (KF<2000 ppm H2O). [0261] This PhMe solution of product was transferred to 250 mL flask with overhead stirring. An addition funnel was charged with 17.5 mL of 5.33 M HCl in IPA (5.3 M), which was added slowly over 20 minutes. The resulting slurry was aged for 30 minutes at Ti=40 C., and then was gradually cooled to Ti=20-22 C. over 30 minutes. After aging for 1 hour, the slurry was slowly cooled to Ti=0 C. over 30 minutes by use of an external bath. After 30 minutes, the slurry was filtered. The cake was washed with 16 mL of cold (Ti=-10 vC) 14:2 PhMe:IPA. The cake was then washed with 15 mL of ambient temperature (Ti=22 C.) MTBE. After drying, 7.6 g of allyl isoindoline was isolated as an off white solid. The isolated product assayed for 98.7 wt %. According to the analysis of related databases, 923590-95-8, the application of this compound in the production field has become more and more popular. Reference:
Patent; Chen, Cheng; Kong, Jongrock; Humphrey, Guy; Dolman, Sarah; Li, Hongmei; Tudge, Matthew T.; Yong, Kelvin; Xiang, Bangping; Zacuto, Michael; US2013/274463; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem