Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate → methyl 7-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate (Intermediate 9, 0.165 g), N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.3 g), tri-tert-butylphosphinium tetrafluoroborate (0.01 g), tris-(dibenzylideneacetone)dipalladium (0.019 g) in dioxane (6 mL) was degassed then heated at 100° C. for 75 minutes. After cooling, the mixture was evaporated to approximately half volume then partitioned between ethyl acetate and water. The organic layer was washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 0-14% to give methyl 7-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate (0.028 g) as a yellow solid.

Provenance & Evidence