Diisopropylethylamine → Methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-ethynyl-5-nitrobenzoate (1.45 g, 7.08 mmol), tert-butyl (3-iodophenyl)carbamate (2.26 g, 7.08 mmol) in THF (28 mL) was treated with bis(triphenylphosphine)palladium(II) chloride (248 mg, 0.354 mmol), copper(I) iodide (108 mg, 0.566 mmol) and N,N-diisopropylethylamine (2.47 mL, 14.2 mmol) and stirred at 25° C. overnight. The reaction was diluted with water and extracted with ethyl acetate three times. The combined organic solutions were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.85 g, 66%). LCMS for C21H20N2O6Na (M+Na)+: m/z=419.3.

Provenance & Evidence