Potassium Carbonate → HCID 57731610, 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 (138.4 mg, 0.274 mmol), 3-amino-6-chloro-pyridazine-4-carboxylic acid dimethylamide (54.9 mg, 0.274 mmol), palladium acetate (3.0 mg, 0.013 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (11.2 mg, 0.0274 mmol) were combined under nitrogen. Acetonitrile (0.5 mL), tetrahydrofuran (0.5 mL) and 1 M aqueous potassium carbonate (0.822 mL, 0.822 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 3-amino-6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide. MS: m/z 543 (M+H+).

Provenance & Evidence