Ethanol → 3-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

1-Tosyl-1H-pyrrolo[2,3-b]pyridin-3(2H)-one (234 mg, 0.815 mmol) was dissolved in ethanol (8 mL). A few drops of concentrated sulfuric acid were added, and the mixture was heated at reflux for 5 hours. The mixture was then allowed to cool to room temperature. The mixture was then diluted with EtOAc, washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated. Flash 40 Biotage (40S cartridge, DCM) afforded 3-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine (126 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 8.42-8.45 m, 1H), 7.95-7.99 (m, 2H), 7.83-7.87 (m, 1H), 7.20-7.25 (m, 2H), 7.11-7.17 (m, 1H), 7.06 (s, 1H), 4.03-4.11 (m, 2H), 2.34 (s, 3H), 1.45-1.50 (m, 3H).

Provenance & Evidence