Sodium Bicarbonate → (5)-tert-butyl 2-(3-(3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl)prop-1-enyl)-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of (5)-tert-butyl 3-(3-allylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (220 mg, 0.52 mmol), tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (297 mg, 0.78 mmol), sodium bicarbonate (435 mg, 5.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) in 4 ml of DMF was heated to 125° C. overnight. The reaction was cooled to room temperature and then filtered through celite. The filtrate was concentrated and the crude product was introduced to a silica gel loading column and purified by column chromatography (30-60% EtOAc/Hexans) to provide the desired product (178 mg, 0.25 mmol), 47%. MS (m/z) 726 [M+H]+.

Provenance & Evidence