Cesium fluoride → 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Participants

Reaction Steps

A mixture of 1-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile (1.25 g, 3.83 mmol), 4-(4,4,5,5-tetramethyl)-1,3-2-dioxaboralanyl-2-yl-aniline (0.96 g, 4.90 mmol), CsF (1.46 g, 9.58 mmol) and Pd(PPh3)2Cl2 (110 mg, 0.15 mmol) in DME (20 mL) was added to a flask and alternatively evacuated and flushed with N2. The reaction was then heated at reflux for 24 h and then cooled to room temperature. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic phases were washed with H2O and saturated NaCl and then dried over MgSO4 and concentrated. The crude reaction mix purified by flash chromatographt on silica gel using EtOAc/CH2Cl2 (5/95) as eluent to afford 765 mg (69%) of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile as a yellow solid.

Provenance & Evidence