Formic Acid → HCID 59425713, compound

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (2.5 mL) and 98% formic acid (1.0 mL) were heated at 65° C. for 1 hour. This was cooled to 0° C. 2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.32 mmol), prepared as in example 1H, was taken up in THF (1.2 mL) and added to the formic acetic anhydride mixture. This was stirred at 0° C. for 30 minutes. The reaction mixture was then partitioned between H2O and EtOAc. The EtOAc layer was washed with saturated NaHCO3, followed by saturated brine. The organic layer was dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/EtOAc) yielded of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-formamide (105 mg, 96%) as a yellow solid.

Provenance & Evidence