Oxalyl chloride → Ethyl 6-chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate

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Reaction Steps

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 50 mg, 0.13 mmol) was diluted with dichloromethane (2 mL) followed by the addition of oxalyl chloride in dichloromethane (2M) (73 μL, 0.15 mmol) and DMF (1 drop). After stirring for 15 minutes, 2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine (31 mg, 0.13 mmol) and diisopropyl ethylamine (69 μL, 0.40 mmol) were added. After stirring for 1 hour, the reaction was loaded onto silica gel and eluted with 100% ethyl acetate to yield ethyl 6-chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (15 mg, 0.025 mmol, 19% yield). MS (es+apci, positive) m/z=589.2.

Provenance & Evidence