Lawesson's reagent → 5-(7-Bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole

Participants

Reaction Conditions

Reaction Steps

To Lawesson's Reagent (1.393 g, 3.44 mmol) was added N-(6-bromo-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 82C, 1.1 g, 2.295 mmol) followed by toluene (10 mL). The reaction mixture was heated at 140° C. behind a safety shield for 15 h. The reaction mixture was cooled to room temperature, loaded onto a silica gel column (with toluene) and purified using hexane/EtOAc (9.25:0.75, 600 mL). The desired fractions were collected and concentrated to yield a pale yellow solid. The solid was triturated with acetonitrile (20 mL), filtered and washed with acetonitrile (2×5 mL) to yield 5-(7-bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (0.935 g, 1.959 mmol, 85% yield) as a pale yellow solid. LC/MS M+1=478.

Provenance & Evidence