Acetone → Ammonia

Participants

Reaction Conditions

Reaction Steps

To a solution of {4-[3-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-indazol-1-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine (0.03 g, 0.074 mmol) in chloroform (1 mL) were added acetone (0.5 mL) and sodium triacetoxyborohydride (0.039 g, 0.18 mmol) and the solution was stirred at 70° C. for 1 h. After cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate. The aqueous layer was back-extracted with methylene chloride (2×). The combined organic extracts were dried (K2CO3), filtered, and concentrated in vacuo. Flash chromatography with 1%, 3%, and 5% 2M NH3 in MeOH/CHCl3 gave the title compound as an off-white glass. MS (ES+): 453.3 [M+H]+, 451.4 [M−H]−.

Provenance & Evidence