Water → (4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

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Reaction Steps

To a suspension of 2-ethoxycarbonyl-4-methoxypyrrolo-[2,3-b]pyridine 3 (1.90 g, 8.62 mmol) in anhydrous THF (25 mL) was added LiAlH4 (0.218 g, 17.2 mmol) in small portions under N2 atmosphere. The mixture was stirred at reflux temperature for 50 min. After cooling, it was poured into cool H2O (20 mL) and extracted with EtOAc (4×15 mL). The combined organic layers were washed with brine (20 mL) and dried (Na2SO4). After filtration, the filtrate was concentrated to dryness and the residue was chromatographed on a silica gel column using 5% methanol in CH2Cl2 to give 4 as white solid. Mp 210-212° C.; Yield: 1.10 g, 71%; ESI MS: m/z 178.9 (M+1).

Provenance & Evidence