Toluene → HCID 69313650, compound

Participants

Reaction Conditions

Reaction Steps

Tris(dibenzylidine acetone)dipalladium CHCl3 (5.0 mg, 0.004 mmol), and potassium carbonate (26 mg, 0.19 mmol) were suspended in 1 mL of toluene under argon. A solution of 6-(2,4-Difluoro-phenoxy)-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (48 mg, 0.09 mmol) in 2 mL toluene was added, and the reaction mixture was stirred at 65° C. for 16 hours, then stirred at 110° C. for four hours. The reaction mixture was cooled, filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (23 mm×14 cm silica with hexanes/EtOAc 20:1 to 4:1) to yield 42 mg of 6-(2,4-Difluoro-phenoxy)-3-styryl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine.

Provenance & Evidence