Tributylvinyltin → 3-Phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole

Participants

Reaction Steps

A mixture of 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl trifluoromethanesulfonate (Preparation 56D, 0.451 g, 0.825 mmol), tributyl(vinyl)tin (0.265 mL, 0.908 mmol), and lithium chloride (0.105 g, 2.476 mmol) in dioxane (5.0 mL) was placed in a microwave reaction vessel. To this was added tetrakis(triphenylphosphine)palladium(0) (0.095 g, 0.083 mmol) and argon was bubbled into the mixture for 3 min. The vessel was capped and the reddish brown mixture was immersed in a 100° C. oil bath. After 6 h of stirring, the reaction mixture was cooled to room temperature. EtOAc was added and the contents were stirred for 30 min. It was then filtered through a plug of Celite. The filter cake was washed with EtOAc (2×). The combined organic layers were then concentrated in vacuo. The residue was suspended in ether and stirred vigorously for another 30 min., filtered through a plug of celite and the filter cake washed with ether (2×). The combined organic layers were concentrated and chromatographed. The product had an LC ret. time=3.996 min. (condition: Start % B=50, Final % B=100, Gradient Time=4 min, Flow Rate=4 ml/min, Wavelength=220, Solvent Pair=MeOH−H2O−TFA; Solvent A=10% MeOH—90% H2O−0.1% TFA; Solvent B=90% MeOH−10% H2O−0.1% TFA; Column 1=1: Waters Sunfire C18 4.6×50 mm (4 min. grad)); LC/MS M+1=425.07.

Provenance & Evidence