Cesium carbonate → N-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-pyridazine-3,6-diamine

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Reaction Conditions

Reaction Steps

A mixture of 2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-ylamine (100 mg, 0.36 mmol), 3-amino-6-chloropyridazine (57 mg, 0.44 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), Xantphos (21 mg, 0.036 mmol) and cesium carbonate (234 mg, 0.72 mmol) in dioxane (2.5 mL) was degassed with argon then heated at 150° C. for 30 minutes in a microwave reactor. The reaction mixture was 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 (4-7% methanol in DCM) to afford the title compound as a beige solid (17 mg, 13% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.45 (d, J=0.9 Hz, 1H), 7.95-7.89 (m, 2H), 7.86-7.84 (m, 2H), 7.76 (dd, J=9.1, 7.2 Hz, 1H), 7.62 (d, J=9.7 Hz, 1H), 7.57-7.53 (m, 1H). LCMS (Method B): RT=2.56 min, m/z: 372 [M+H+].

Provenance & Evidence