Trifluoroacetic acid → 3-ethyl-1H-pyrrolo[2,3-c]pyridine

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Reaction Steps

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (1.53 g, 9.55 mmol) in TFA (29 mL) triethylsilane (6.88 g, 59.21 mmol) is added and stirred at rt for 18 h. The mixture is concentrated and extracted with EtOAc. The organic layer is washed with 2 N aqueous KOH, dried (Na2SO4), filtered and evaporated. The residue is chromatographed through silica gel eluting with 10% MeOH in DCM to afford 3-ethyl-1H-pyrrolo[2,3-c]pyridine (1.35 g, 97%). MS: 147 (M+H); 1H NMR (300 MHz, CDCl3): δ 13.3 (broad, N—H) 9.46 (s, 1H), 8.04 (s, 1H), 7.71-7.88 (m, 2H), 2.88 (q, 2H), 1.39 (t, 3H).

Provenance & Evidence