Diethylamine → {5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

A 500 mL round bottom flask was charged with methyl-pent-4-ynyl-carbamic acid tert-butyl ester (1.70 g, 8.62 mmol), 4-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide (3.0 g, 7.53 mmol), copper iodide (0.225 g, 1.18 mmol), palladium tetrakistriphenylphosphine (0.93 g, 0.805 mmol), and diethylamine (258 mL) and the resulting mixture stirred at room temperature for 24 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF40-400 g column, gradient 90:10-10:90 Heptane:EtOAc) to yield {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester. MS (ES+) 468 (M+1).

Provenance & Evidence