Dimethylformamide → 1H-Indol-1-amine, 6-(trifluoromethyl)-

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (6.5 g, 162 mmol, 60% in mineral oil) in DMF (54 mL) at 0° C. is treated with 6-trifluoromethylindole (2.0 g, 10.8 mmol) and stirred at 0° C. for 0.5 h. The mixture is treated with HOSA (6.1 g, 54 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 Et2O (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 6-trifluoromethyl-indol-1-ylamine (1.79 g, 83%). MS: 201 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.74 (s, 1H), 7.67 (d, 1H), 7.35 (d, 1H), 7.30 (m, 1H), 6.45 (d, 1H), 4.83 (s, NH2, 2H).

Provenance & Evidence