Bromide ion → HCID 10363337, compound

Participants

Reaction Steps

Part B: 6-(3-Hydroxy-propyl)-1-(4-methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (0.200 g, 0.542 mmol) and phosphorus tribromide (0.077 mL, 0.812 mmol) were dissolved in methylene chloride (20 mL) and stirred at rt for 2 hr. The reaction was quenched with water (100 mL), extracted with methylene chloride (3×100 mL), washed with saturated NaHCO3 (1×100 mL), washed with brine (1×100 mL), dried over Na2So4, and concentrated to afford 0.096 g (41%). The bromide intermediate (0.048 g, 0.111 mmol) was redissolved in methylene chloride (6 mL), and 2M dimethylamine (0.389 mL, 0.777) was added. The reaction was stirred at rt overnight. The reaction was evaporated, redissolved in toluene (15 mL), and re-concentrated. Purification was performed by reverse phase HPLC and freeze-dried to afford the title compound (0.014 g, 32%): 1H NMR (CDCl3) δ 7.43 (d, j=8.8 Hz, 2H), 6.96 (d, j=9.1 Hz, 2H), 3.85 (s, 3H), 3.71 (t, j=7.0 Hz, 2H), 3.56 (t, j=6.6 Hz, 2H), 3.08–2.98 (m, 4H), 2.80(s, 6H), 2.15–2.02 (m, 2H) ppm; Mass Spec 397.4(M+H)+.

Provenance & Evidence