3-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine → [2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of {2-[3-(4-bromo-2-dimethylcarbamoyl-phenyl)-ureido]-ethyl}-methyl-carbamic acid tert-butyl ester (75 mg, 0.17 mmol), 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 (85 mg, 0.168 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloromethane adduct (13.7 mg) was dissolved in a mixture of acetonitrile (4 mL), 1 M aqueous sodium carbonate (4 mL) and tetrahydrofuran (1 mL). The mixture was irradiated in the microwave to 120° C. for 10 minutes. The reaction mixture was then concentrated and the residue was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (0 to 100% [10% methanol in ethyl acetate] in hexanes) to give 84 mg (66%) of [2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester. MS: m/z 741.5 (M+H+).

Provenance & Evidence