2-Methyltetrahydrofuran → 5-(3,5-Dimethylisoxazol-4-yl)-3-hydroxy-7-methoxy-3-phenylindolin-2-one

Participants

Reaction Steps

A suspension of 5-(3,5-dimethylisoxazol-4-yl)-7-methoxyindoline-2,3-dione (45 mg, 0.165 mmol) and anhydrous THF (1.5 mL) was added dropwise a solution of phenylmagnesium bromide in 2-methyltetrahydrofuran (2.9 M/L, 0.3 mL, 0.87 mmol). The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with EtOAc (30 mL), washed with saturated aqueous NH4Cl (10 mL), brine (3×10 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, purified by pre-TLC (CH2Cl2:EtOAc=3:2) to give the desired product as a light brown solid (28 mg, 48%). 1H NMR (400 MHz, DMSO-d6). δH 10.56 (s, 1H), 7.31-7.32 (m, 5H), 6.95-6.96 (m, 1H), 6.69-6.71 (m, 2H), 3.89 (s, 3H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 351.

Provenance & Evidence