Ammonium Hydroxide → HCID 18446617, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-1-[3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-2-yl]ethanone (250 mg, 0.75 mmol) in N,N-dimethylformamide (15 mL) was added thioacetamide (67 mg, 0.90 mmol). After heating at 60° C. for 3 hours, the reaction was cooled to room temperature. An ammonium hydroxide solution was used to adjust the pH to 9. The resultant solution was extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over magnesium sulfate. Filtration and concentration gave 3-(2-fluoro-4-pyridinyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridine (220 mg, 95%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.56 (d, 1H), 8.23 (d, 1H), 7.61 (d, 1H), 7.30 (s, 1H), 7.27 (m, 2H), 7.05 (s, 1H), 6.89 (m, 1H), 2.76 (s, 3H). MS m/z 311 (M+1).

Provenance & Evidence