Ammonium Chloride → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

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Reaction Steps

A solution of 4-chloro-6-iodo-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (41.39 g, 86.6 mL, Intermediate 62: step c) in THF (800 mL) was cooled to 4° C., and isopropylmagnesium chloride (44.2 mL, 88.4 mmol, 2 M in THF) was added over 10 min. The mixture was stirred for 20 min and then N-methoxy-N,1-dimethyl-1H-1,2,3-triazole-5-carboxamide (14.74 g, 86.6 mmol, Intermediate 61) in THF (150 mL) was added. After warming to room temperature and stirring for 15 h, a solution of aqueous ammonium chloride (900 mL, 13 wt %) was added. The resulting biphasic mixture was stirred for 15 min. The layers were then separated, and the organic layer was washed with brine (450 mL). The organic layer was diluted with heptane (500 mL) and stirred for 1 h. The resulting suspension was filtered, washed with heptane (100 mL), and dried in a 60° C. vacuum oven to afford the title compound as a white solid.

Provenance & Evidence