Lawesson's reagent → HCID 67171557, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 56A, 337 mg, 0.783 mmol) and Lawesson's reagent (2,4-Bis-[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetane 2,4-disulfide) (475 mg, 1.175 mmol) in THF (4.0 ml) was heated for 33 min at 140° C. on a microwave which resulted in an incomplete reaction. The reaction mixture was then microwaved for 15 min more at 140° C. The crude reaction mixture was loaded onto a 40 g silica gel Redisep® cartridge which was presaturated with 10% EtOAc-hexanes and eluted with the same. The 5-(7-methoxy-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (0.365 g, 0.852 mmol, quant. yield) was isolated as a yellow solid. The product had an LC ret. time=2.62 min. (condition: Start % B=0; Final % B=100; Gradient Time=2 min; Flow Rate=5 ml/min; Wavelength=220; Solvent Pair=MeOH/H2O/TFA; Solvent A=0.1% TFA in MeOH: H2O (10:90); Solvent B=0.1% TFA in; MeOH: H2O (10:90); Column 1=Waters Sunfire C18 5 um 4.6×30 mm); LC/MS M+1=429.04.

Provenance & Evidence