Potassium Carbonate → HCID 69447259, compound

Participants

Reaction Steps

A mixture of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (969 mg, 3.4 mmol) and potassium carbonate (9.6 g, 69.4 mmol) in n-butylamine (20 mL) was heated to reflux for 5 hours. The mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in ethyl acetate and water. The organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over sodium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes-ethyl acetate) provided 1-[7-(butylamino)-2-(4-fluorophenyl)pyrazolo[1 ,5-α]pyridin-3-yl]ethanone (921 mg, 84%) as a tinted oil. 1H NMR (CDCl3): δ 7.71 (d, 1H), 7.63 (dd, 2H), 7.49 (t, 1H), 7.23 (t, 2H), 6.16 (d, 1H), 6.10 (m, 1H), 3.40 (m, 2H), 2.18 (s, 3H), 1.78 (m, 2H), 1.52 (m, 2H), 1.02 (t, 3H); MS m/z 326 (M+1); Rf 0.6 (1:1 hexanes:ethyl acetate).

Provenance & Evidence