3H-IMidazo[4,5-b]pyridine-6-Methanol synthesis

Yield:1022158-37-7 15%

Reaction Conditions:

Stage #1: 1H-imidazo[4,5-b]pyridine-6-carboxylic acidwith lithium aluminium tetrahydride in tetrahydrofuran at -78 - 20;
Stage #2: with methanol in tetrahydrofuran;

Steps:

5.1.123.A

A. (lH-Imidazo[4,5-b]pyridin-6-yl)methanol.; Imidazo[4,5-b]pyridine-6- carboxylic acid (2.02 g, 12.38 mmol) was suspended in anhydrous tetrahydrofuran (100 mL) and cooled -78 ⁰C. A solution of lithium aluminum hydride (2.0M, 24.7 mL, 49.5 mmol) was added and the reaction was allowed to slowly warm to room temperature, with stirring, overnight. The reaction was quenched with methanol and the crude product adsorbed onto silica gel. Flash Chromatography (30% MeOH in EtOAc) afforded the title compound (0.29 g, 1.95 mmol, 15%) as a white solid. MS (ESI) m/z 150.1 [M+ 1]⁺.

References:

WO2008/51494,2008,A1 Location in patent:Page/Page column 161