Dimethylformamide → 3-ethyl-5-trifluoromethoxy-1H-indol-1-ylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (7.9 g, 197 mmol, 60% in mineral oil) in DMF (60 mL) at 0° C. is treated with 3-ethyl-5-trifluoromethoxy-1H-indole (3 g, 13.1 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (7.4 g, 65.5 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice and filtered through a pad of Celite. The filtrate is extracted with heptane (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10%-30% EtOAc in heptane to afford 3-ethyl-5-trifluoromethoxy-indol-1-ylamine (2.05 g, 64%). MS: 245 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.37 (m, 2H), 7.11 (m, 1H), 7.00 (s, 1H), 4.72 (s, NH2, 2H), 2.73 (q, 2H), 1.29 (t, 3H).

Provenance & Evidence