Phosgene → HCID 66606918, compound

Participants

Reaction Conditions

Reaction Steps

(2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.203 g, 0.51 mmol) and diisopropylethylamine (0.22 mL, 1.28 mmol) were combined in CH2Cl2 (2 mL) and cooled to 0° C. Phosgene (20% in toluene; 0.41 mL, 0.77 mmol) was added, and the reaction was stirred for 2.5 hours. After warming to room temperature, 2-(aminomethyl)pyridine (0.08 mL, 0.77 mol) was added, followed by triethylamine (0.14 mL, 1.02 mmol), and the reaction was stirred for 30 minutes. Analytical LCMS indicated that some starting material was still present, so additional triethylamine (0.07 mL, 0.51 mmol) was added, and the reaction was stirred for 45 minutes. The mixture was diluted with CH2Cl2 and H2O, and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried and concentrated, and the residue was purified by silica gel chromatography (40-100% EtOAc in hexanes) to give the title compound.

Provenance & Evidence