Potassium Carbonate → HCID 86623947, compound

Participants

Reaction Conditions

Reaction Steps

3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (938 mg, 3.02 mmol), (6-Chloro-pyrazin-2-yl)-acetic acid ethyl ester (605 mg, 3.02 mmol), palladium acetate (20.8 mg, 0.093 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (76.3 mg, 0.186 mmol) were combined under nitrogen. Acetonitrile (10 mL) and 1 M potassium carbonate (5.5 mL, 5.5 mmol) were added and the vial was flushed with nitrogen, capped and heated at 80° C. for 15 h. The layers were separated. The organics were diluted with ethyl acetate and washed with brine (1×), dried over sodium sulfate and adsorbed onto silica gel. The material was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford {6-[3-(2-methoxyphenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl-acetic acid ethyl ester (1.05 g, 64%). MS: m/z 453 (M+H+).

Provenance & Evidence