Electric Literature of 912999-79-2, 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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.
A mixture of Compound 151A (340 mg, 2.36 mmol) and 1-(azidomethyl)-4- methoxybenzene (500 mg, 3.07 mmol) in toluene (15 mL) was stirred at 110 C for 48 hours. The reaction mixture was concentrated and purified by column chromatography on silica gel using ethyl acetate- hexane as eluent to afford a Mixture 151B. LC-MS (ESI) m/z: 278 [M+H]._A Mixture 151B (60 mg, 0.217 mmol) and thionyl chloride (0.45 mL) in methylene chloride (10 mL) was stirred at 50 C for 5 hours. The reaction mixture was concentrated to give isic, which was used directly in the next step without further purification.LC-MS (ESI) m/z: 296 [M+H]._ A Mixture 151C (74 mg, 0.2 17 mmol), 5-chloroisoindoline (38 mg, 0.248 mmol), and K2C03 (60 mg, 0.43 5 mmol) in DMF (6 mL) was stirred at 60 C for 5 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC to afford a Mixture 151D. LCMS (ESI) m/z: 413 [M+H]t
The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline hydrochloride. I believe this compound will play a more active role in future production and life.
Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem