Potassium Carbonate → N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-methylphenyl}-2,2,2-trifluoroacetamide

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Reaction Steps

To a solution of N-{5-[(2-chloro-4-pyrimidinyl)ethynyl]-2-methylphenyl}-2,2,2-trifluoroacetamide (2.7 g, 8 mmol) in DMF (50 mL) was added N-aminopyridinium iodide (3.6 g, 16 mmol) and K2CO3 (3.3 g, 24 mmol). After 3 h, the reaction was diluted with water and extracted with DCM. The combined organic solutions were dried over MgSO4 and concentrated onto silica gel. The crude material was purified by column chromatography. Fractions containing product were concentrated and the solid triturated with DCM and hexanes to give 1.92 g of the desired product (56%). 1H NMR (400 MHz, d6-DMSO) δ 11.07 (s, 1H), 8.89 (d, J=6.8 Hz, 1H), 8.45 (d, J=6.8 Hz, 1H), 8.40 (d, J=8.8 Hz, 1H), 7.65-7.61 (m, 1H), 7.55 (s, 1H), 7.52-7.49 (m, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.22-7.19 (m, 1H), 7.08 (d, J=5.6 Hz, 1H), 2.27 (s, 3H) ppm.

Provenance & Evidence