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

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 7, 0.378 g), N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine (Intermediate 3, 0.41 g), tri-tert-butylphosphinium tetrafluoroborate (0.023 g), tris-(dibenzylideneacetone)dipalladium (0.036 g) in dioxane (6 mL) and DMSO (0.6 mL) was sealed in a microwave vial, under nitrogen and heated at 150° C. in the microwave for 45 minutes. After cooling, the mixture was diluted with ethyl acetate and water, the organic layer was separated, 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 0-10% to give methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (0.13 g) as a brown foam. This material was used without further characterisation.

Provenance & Evidence