Tri-tert-butylphosphine tetrafluoroborate → t-butyl N-(3-cyclopentyloxy-4-methoxyphenyl)-N-(2-(3-pyridyl)ethyl)-3-aminobenzoate

Participants

Reaction Steps

To a mixture of 103 mg of 1-butyl N-(2-(3-pyridyl)ethyl)-3-aminobenzoate (0.35 mmol) and 200 mg of 3-cyclopentyloxy-4-methoxyiodobenzene (0.63 mmol) in 5 mL of toluene was added 100 mg of sodium t-butoxide (1.0 mmol), 15 mg of tri-t-butylphosphonium tetrafluoroborate (0.05 mmol) and 25 mg of tris(dibenzylidineacetone)dipalladium(0) (0.028 mmol). The mixture was stirred for 16 h and filtered through celite. The celite was washed with 3×5 mL of toluene and the filtrate was concentrated in vacuo. The residue was purified by column chromatography using 30%-40% EtOAc in hexanes as eluant to give 48 mg of t-butyl N-(3-cyclopentyloxy-4-methoxyphenyl)-N-(2-(3-pyridyl)ethyl)-3-aminobenzoate.

Provenance & Evidence