Hydrochloric Acid → 2-Hydroxy-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetonitrile

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Reaction Steps

To 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazole-7-carbaldehyde (Preparation 84A, 0.175 g, 0.410 mmol) in dichloromethane (5 mL) was added zinc iodide (0.039 g, 0.123 mmol) followed by trimethylsilyl cyanide (0.083 mL, 0.616 mmol) over a period of 1 min. at room temperature. The reddish-brown reaction mixture was stirred at room temperature for 1 h. The reaction mixture was cooled to 0° C. and conc. HCl (0.068 mL, 0.821 mmol) was added over a period of 1 min. and the contents stirred at room temperature for 5 min. The reaction mixture was partitioned between dichloromethane (2×20 mL) and 10% aq. Na2S2O3 (10 mL). The dichloromethane layer was dried over sodium sulfate and concentrated to yield 2-hydroxy-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetonitrile (0.185 g, 0.408 mmol, 99% yield) as a yellow solid. LC/MS M+1=454.

Provenance & Evidence