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