Tri-tert-butylphosphine tetrafluoroborate → HCID 56656346, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-(2-bromo-4-fluorobenzenesulfonylamino)-4-oxo-4,5-dihydrofuro[2,3-c]quinoline-6-carboxylic acid (Intermediate 86, 0.190 g), N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.476 g), tris-(dibenzylideneacetone)dipalladium (0.043 g) and tri-tert-butylphosphonium tetrafluoroborate (0.023 g) in dioxane (5 mL) was heated under argon to 80° C. in a sealed vessel for 1 hour. The hot reaction mixture was filtered through Celite and washed with dioxane, ethyl acetate and acetonitrile. The filtrate was concentrated in vacuo and the residue was triturated with water and acetonitrile and then acetone. The solid was collected by filtration, dissolved in DMSO and filtered. The filtrate was purified by HPLC (C18) eluting with a mixture of acetonitrile and water, containing 0.1% formic acid, with a gradient of 25-75% acetonitrile, to give 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4-oxo-4,5-dihydrofuro[2,3-c]quinoline-6-carboxylic acid (0.062 g).

Provenance & Evidence