Tributylvinyltin → HCID 67168124, compound

Participants

Reaction Conditions

Reaction Steps

To a heterogeneous solution of 7-bromo-5-methyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydroisoxazolo[4,3-c]quinoline (Preparation 77E, 0.040 g, 0.084 mmol) in dioxane (5.0 mL) in a sealed tube was added sequentially tributyl(vinyl)stannane (0.027 mL, 0.092 mmol) and lithium chloride (10.7 mg, 0.252 mmol). The reaction mixture was degassed with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (9.71 mg, 8.40 μmol) was added, and the stirred reaction mixture was heated in an oil bath at 100° C. for 4 h overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with dichloromethane (10 mL), filtered through a pad of Celite, and rinsed with dichloromethane (10 mL). The filtrate was concentrated, and the solid residue was purified by flash silica gel chromatography using a 5% mixture of ethyl acetate in hexane to give the crude product mixture. The crude mixture 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 give 5-methyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydroisoxazolo[4,3-c]quinoline [0.020 g, 0.047 mmol, 56%] as a viscous, tan film. The product had an HPLC ret. time=3.85 min. (condition B); LC/MS M+1=424.1.

Provenance & Evidence