Potassium Carbonate → HCID 22474689, compound

Participants

Reaction Steps

A solution of ethyl 4-chloro-1-methyl-6-trifluoromethanesulfonyloxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (387 mg, 1 mmol) in THF is treated with tetrakis(triphenyl phosphine) palladium (115 mg, 10 mol %), stirred for 20 min at room temperature, treated sequentially with 3,5-dichlorobenzeneboronic acid (285 mg, 1.5 mmol), 2N K2CO3 (0.7 mL) and benzyl triethyl ammonium chloride (319 mg, 1.4 mmol), heated at reflux temperature for 4 h, cooled to room temperature and diluted with EtOAc. The phases are separated and the organic phase is washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, hexanes:EtOAc, 5:1) to afford the title product as a white solid, 127 mg (33% yield), identified by HNMR analysis.

Provenance & Evidence