Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 mixture of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd (OAc) 2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH : DMSO (1: 1,4 mL) was stirred for 16 h under CO (balloon) at 80 C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2 x 25 mL). The organic layer was dried (Na2S04), concentrated and purified by silica gel column chromatography (eluent = 20% EtOAc-Hexane), giving pure 1, 3-dihydro-isoindole-2,5- dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81 %). MS (APCI+) : m/z 178.1 (MH+-Boc).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-bromoisoindoline-2-carboxylate, its application will become more common.
Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem