Dimethylformamide → 3-Ethyl-5-trifluoromethyl-indol-1-ylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (7 g, 176 mmol, 60% in mineral oil) in DMF (50 mL) at 0° C. is treated with 3-ethyl-5-trifluoromethyl-1H-indole (2.4 g, 11.3 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (6.6 g, 59 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, filtered through a pad of Celite, and extracted with EtOAc (3×150 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10%-50% EtOAc in heptane to afford 3-ethyl-5-trifluoromethyl-indol-1-ylamine (1.3 g, 50%). MS: 229 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.84 (s, 1H), 7.45 (s, 2H), 7.02 (s, 1H), 4.74 (s, NH2, 2H), 2.77 (q, 2H), 1.31 (t, 3H).

Provenance & Evidence