Sodium Carbonate → HCID 57537513, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5-Bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (400 mg, 1.54 mmol), bis(pinacol)diborane (431 mg, 1.7 mmol), potassium acetate (454 mg, 4.6 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (25 mg, 0.03 mmol) in dimethylacetamide (2 mL) was stirred under nitrogen at 120° C. for 12 h. 5-Bromo-3-(2-methoxy-phenyl)-4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (491 mg, 1.05 mmol), sodium carbonate solution (2M in water, 2.3 mL, 4.6 mmol), dimethylacetamide (2 mL) and additional 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (30 mg, 0.035 mmol) was added and the mixture was stirred for an additional 2 h at 120° C. Sodium sulfate was added to the crude reaction mixture and the solids were filtered over Celite. The solids were rinsed with ethyl acetate and acetonitrile and the combined filtrate was concentrated. The resulting oil was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (202 mg, 0.35 mmol, 34% yield; and 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-acetamide.

Provenance & Evidence