Water → 4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

4-(benzyloxy)-6-bromopyrazolo[1,5-a]pyridine (200 mg, 0.660 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (412 mg, 1.979 mmol), tetrakis(triphenylphosphine)palladium (0) (76 mg, 0.066 mmol), and sodium carbonate (210 mg, 1.98 mmol) were suspended in 1,4-dioxane (4 ml)/water (0.444 ml). The mixture was sparged with argon for 10 minutes, then heated to 90° C. for 2 h. After cooling to ambient temperature, the reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to afford 4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine contaminated with triphenylphosphine oxide.

Provenance & Evidence