Hydrochloric Acid → C-[3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridin-7-yl]-methylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile (477 mg, 1.0 mmol, prepared according to Example 35, Step 20.2) in anhydrous THF (12 mL) were added a BH3.THF complex (1.0 M solution in THF, 4.5 mL, 4.5 mmol) followed by a 4M HCl solution in dioxane (10 drops) at RT. The reaction mixture was heated at 50° C. and stirred for 3 h, then cooled to 0° C. (ice bath), quenched by the cautious addition of a 2M HCl solution in water (10 mL) and poured into water (100 mL). The aqueous mixture was washed with Et2O (2×30 mL) then basified to pH 10 by the addition of a 2M Na2cO3 solution in water and extracted with DCM (2×30 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated to dryness to yield the crude C-[3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridin-7-yl]-methylamine intermediate.

Provenance & Evidence