N-methyl-2-pyrrolidone → HCID 68556731, compound

Participants

Reaction Steps

NaH (60%, 60 mmol) is portion-wise added to a solution of 5-cyano-1H-indole (20 mmol) in NMP (35 mL), and the reaction mixture is 0° C. for 1 h. A solution of HOSA (60 mmol) in NMP (14 mL) is added drop-wise at 0° C. The reaction mixture is warmed to rt and stirred overnight, then quenched with water and extracted with EtOAc. The organic layer is separated, washed with water three times and with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 20-40% EtOAc in heptane to afford 5-cyano-indole-1-ylamine (531 mg, 16%) as a solid. 1H NMR (300 MHz, CDCl3): δ 4.88 (br, 2N—H), 6.53 (d, H), 7.32 (d, H), 7.54 (q, 2H), 7.98 (d, H).

Provenance & Evidence