Dimethylformamide → HCID 67198451, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid methyl ester (1.50 g, 4.30 mmol), Pd2(dba)3 (393.5 mg, 0.43 mmol), Zn(CN)2 (622 mg, 5.30 mmol), dppf (249.48 mg, 0.45 mmol) and Zn (196.11 mg, 3.00 mmol) in DMF (30 mL) is degassed with argon for 5 minutes. The mixture is warmed at 120° C. After 3 hours, the mixture is diluted with saturated aqueous ammonium chloride (30 mL) and extracted with EtOAc. The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc-hexanes (20:80) to afford 6-cyano-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid methyl ester.

Provenance & Evidence