Tributylvinyltin → HCID 67171996, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5,5-difluoro-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl trifluoromethanesulfonate (Preparation 66E, 0.024 g, 0.042 mmol) and lithium chloride (2.60 μL, 0.127 mmol) in dioxane (5.0 mL) was degassed with nitrogen for 15 minutes. To the reaction mixture was added tributyl(vinyl)stannane (0.015 g, 0.047 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (4.90 mg, 4.24 μmol) at room temperature. The resulting reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and filtered. The brownish residue was washed with ethyl acetate (3×10 mL), and the combined filtrates were concentrated in vacuo. The residue was chromatographed using reverse-phase preparative HPLC (Column: LUNA 5 u C18, 21×100 mm:Solvent MeOH(B)—H2O(A), 0.1% TFA: 0% B-100% B, Gradient Time 12 min, Stop Time 20 min, Flow Rate 20 ml/min, Wavelength 220 nM) to yield 5,5-difluoro-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (0.012 g, 0.027 mmol, 63.7% yield) as a tan viscous liquid. The product had an HPLC ret. time=3.77 min. (condition B). LC/MS M+1=444.20. 1H NMR (500 MHz, CD3OD) δ ppm 7.75 (1H, d, J=7.93 Hz), 7.55-7.68 (2H, m), 7.38-7.57 (4H, m), 7.18-7.38 (1H, m), 6.63 (1H, dd, J=17.70, 10.99 Hz), 5.75 (1H, d, J=17.70 Hz), 5.19 (1H, d, J=10.99 Hz), and 2.85-3.02 (2H, m).

Provenance & Evidence