Tri-tert-butylphosphine tetrafluoroborate → methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 8-(2-bromo-4-fluorobenzenesulfonylamino)-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 21, 0.088 g), N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (Intermediate 3, 0.222 g), tris-(dibenzylideneacetone)dipalladium (0) (0.020 g) and tri-tert-butylphosphonium tetrafluoroborate (0.01 g) in dioxane (3 mL) was de-gassed and purged with nitrogen and then heated to 80° C. in a sealed vessel for 2 hours. The resultant mixture was cooled, filtered through Celite and washed with ethyl acetate. The filtrate was concentrated in vacuo 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 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate (0.057 g) as a glass.

Provenance & Evidence