Ammonium Acetate → 1-[8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-yl]ethanamine

Participants

Reaction Conditions

Reaction Steps

1-[8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-yl]ethanone (0.12 g, 0.42 mmol) and ammonium acetate (0.32 g, 4.2 mmol) were stirred in methanol (4.6 mL) and heated to 65° C. for 1 hour. Sodium cyanoborohydride (78 mg, 1.3 mmol) was added and the mixture was heated at 65° C. for 16 hours. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (51 mg, 42%). LCMS calculated for C15H14ClFN3 (M+H)+: m/z=290.1. found: 290.0. 1H NMR (300 MHz, DMSO-d6): δ 7.63 (m, 2H), 7.41 (m, 3H), 7.35 (m, 2H), 3.60 (m, 1H), 1.18 (m, 3H).

Provenance & Evidence