Category: 923590-95-8

Synthetic Route of 923590-95-8, 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.

4-Bromoisoindoleline hydrochloride (174 mg, 0.74 mmol) and triethylamine (158.1 mg, 1.56 mmol) were added to a round bottom flask, DMF was dissolved, and stirred for 10 minutes.The final product 03 (80 mg, 0.25 mmol) was added and stirred at 50 C overnight.The reaction was completed and purified by HPLC to give 100 mg of a colorless oily compound.

The synthetic route of 4-Bromoisoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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.

To a solution of (2S,4R)-BOC-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+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.

Reference:
Patent; Holloway, M. Katharine; Liverton, Nigel J.; Ludmerer, Steven W.; McCauley, John A.; Olsen, David B.; Rudd, Michael T.; Vacca, Joseph P.; McIntyre, Charles J.; US2007/27071; (2007); 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. 923590-95-8

Step 1: preparation of benzyl 4-bromoisoindoline-2-carboxylate (compound 3a) To a solution of 4-bromoisoindoline hydrochloride (235 mg, 1.0 mmol) in THF (4 mL) was added TEA (355 mg, 0.49 mL, 3.5 mmol). The mixture was then cooled with ice-water bath. CbzCl (256 mg, 0.22 mL, 1.5 mmol) was added dropwise. The reaction mixture was stirred at rt overnight, then diluted with water (20 mL), and extracted with EtOAc (30 mL) twice. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to afford compound 3a (255 mg) as a pink solid. MS: calc’d 332&334 (MH+), measured 332&334 (MH+).

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

Reference:
Patent; F. Hoffmann-La Roche AG; The designation of the inventor has not yet been filed; (99 pag.)EP3623369; (2020); 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. 923590-95-8

Step a To a stirred solution of 4-bromoisoindoline hydrochloride (CAS Number 923590-95-8; 0.1 g, 0.426 mmol) in l,4-dioxane:water (5: 1; 6 ml) were added phenylboronic acid (0.078 g, 0.64 mmol) and K2C03 (0.176 g, 1.279 mmol) at rt. The reaction mixture was degassed with nitrogen for 10 min. Pd(PPh3)4 (0.024 g, 0.021 mmol) was added to the reaction and reaction mixture was heated at 100C for 16 h. The resulting reaction mixture was cooled to rt and combined with 2 other batches prepared on the same scale by an identical method. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (2 x 20 ml). The combined organic phase was separated, dried over Na2S04, filtered and evaporated to dryness. The residue was re-dissolved in EtOAc (2 ml) and 4M HC1 in 1,4- dioxane (0.3 ml) was added at 0C. The mixture was stirred at rt for 30 min. The excess of solvent was distilled under vaccum and residue was triturated with diethyl ether (10 ml) and EtOAc (10 ml) yielding 4-phenylisoindoline hydrochloride (0.1 g, 0.512 mmol). This material was used for the next step without further purification. LCMS: Method A, 1.731 min, MS: ES+ 196.44; NMR (400 MHz, DMSO-d6) delta ppm 9.84 (br, s, 1H), 7.42 – 7.60 (m, 8 H), 4.49 – 4.63 (m, 4 H).

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; 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

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. 923590-95-8 name is 4-Bromoisoindoline hydrochloride, 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. 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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisoindoline hydrochloride, and friends who are interested can also refer to it.

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