Aluminium lithium hydride → (5-Fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol

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Reaction Conditions

Reaction Steps

To an oven-dried 200 mL round bottom flask equipped for stirring was added methyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (2.4 g, 12.36 mmol) under nitrogen. THF (100 mL) was added and the colorless solution was cooled to 0° C. Lithium aluminum hydride (27.2 mL, 27.2 mmol) was added and the solution was stirred at 0° C. for 3 h. The reaction was quenched with EtOAc (100 mL); brine (100 mL) was added, and the aqueous phase was extracted three times with EtOAc. The organics were dried over Na2SO4 and concentrated to afford the title compound as a yellow fine powder (2.01 g, 98%). 1H NMR (400 MHz, CD3OD) δ 4.96 (d, J=1.26 Hz, 2 H) 6.72 (d, J=3.54 Hz, 1 H) 7.44 (d, J=3.54 Hz, 1 H) 8.06 (d, J=2.78 Hz, 1 H). [M+H] calc'd for C8H7FN2O, 167; found, 167.5.

Provenance & Evidence