3-Bromo-1,1,1-trifluoro-2-propanone → AZD7118 Bromo Trifluoromethyl

Participants

Reaction Conditions

Reaction Steps

3-Bromo-1,1,1-trifluoropropan-2-one (2.260 mL, 21.77 mmol) was added to a mixture of 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 42, 1.1 g, 3.63 mmol) in acetonitrile (25 mL), and the reaction mixture was heated at 80° C. for 4 h. After a clear solution resulted within an hour, and the solution was concentrated under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, then concentrated under reduced pressure to give light yellow solid, which was purified by normal phase column chromatography (silica, 2% MeOH in dichloromethane to 5% MeOH in dichloromethane) to give the title compound as a white solid (470 mg). MS (ESP): 414 (M+1) for C12H12BrF3N4O2S; NMR: 1.06 (t, 3H); 3.12-3.18 (m, 2H); 3.60 (dd, 1H); 3.90 (dd, 1H); 7.13 (brs, 1H); 7.98 (s, 1H); 8.47 (s, 1H); 9.41 (s, 1H).

Provenance & Evidence