Cesium carbonate → [7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

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Reaction Steps

A suspension of 4,7-dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (317 mg, 0.75 mmol), 6-methylpyrimidin-4-ylamine (90 mg, 0.83 mmol), Pd2(dba)3 (17 mg, 0.019 mmol), Xantphos (43 mg, 0.075 mmol) and cesium carbonate (489 mg, 1.5 mmol) in dioxane (11 mL) was sealed in a microwave vial, purged with nitrogen, and irradiated in a microwave reactor at 150° C. for 1 hour. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (50-60% ethyl acetate in cyclohexane), to afford the title compound as a yellow solid (215 mg, 64% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.80 (s, 1H), 9.29 (s, 1H), 8.72 (d, J=1.3 Hz, 1H), 8.40 (s, 1H), 8.17 (s, 1H), 7.85 (d, J=0.9 Hz, 1H), 7.82 (s, 1H), 7.74 (dd, J=7.1 and 9.0 Hz, 1H), 2.46 (s, 3H). LCMS (Method B): RT=3.60 min, m/z: 449 [M+H+].

Provenance & Evidence