Triethylsilane → 3-Ethyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a solution of 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-ethanone (1.34 g, 8.38 mmol) in TFA (25 mL) is added triethylsilane (6.09 g, 52.4 mmol) and stirred at rt for 18 h. The mixture is concentrated, diluted with 2 N aqueous KOH solution and extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and evaporated. The resulting residue is chromatographed through silica gel eluting with 10% MeOH in DCM to afford 3-ethyl-1H-pyrrolo[2,3-b]pyridine (0.91 g). MS: 147 (M+H); 1H NMR (300 MHz, CDCl3): δ 9.23 (broad s, 1H), 8.32 (d, 1H), 7.94 (s, 1H), 7.05-7.14 (m, 2H), 2.80 (q, 2H), 1.35 (t, 3H).

Provenance & Evidence