Water → HCID 86694700, compound

Participants

Reaction Steps

A mixture of 5-fluoro-1-(tripropylsilyl)-1H-indole-4-carboxylic acid (500 mg, 1.49 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (851 mg, 2.24 mmol), and TEA (452 mg, 4.48 mmol) in DMF (5 mL) was stirred at RT for 1 hour. To the mixture was added ammonia water (1 mL), followed by stirring at RT overnight. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography using petroleum ether/EtOAc (2:1) as eluting solvents to afford 5-fluoro-1H-indole-4-carboxamide as a white solid (260 mg, 52.2%). MS (ESI): m/z=179.2 [M+1]+.

Provenance & Evidence