Triethylamine → [5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid (R)-1-(3-trifluoromethyl-phenyl)-ethyl ester

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Reaction Conditions

Reaction Steps

In a 20 ml, vial, 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (114.3 mg, 405 μmol), (R)-1-(3-(trifluoromethyl)phenyl)ethanol (84.8 mg, 446 μmol) and triethylamine (90.2 mg, 124 μL, 891 μmol) were combined with toluene (5 mL) to give a colorless solution and to this was added DPPA (167 mg, 131 μL, 608 μmol). The reaction vial was sealed, heated in a dry block at 65° C. for 3 hr, and allowed to cool to room temperature overnight. The reaction was concentrated, dried from DCM/hexanes, dissolved in minimal DCM and purified by flash chromatography (silica gel, 0% to 60% EtOAc in hexanes). Appropriate fractions were combined, concentrated, dried from DCM/hexanes to yield [5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-carbamic acid (R)-1-(3-trifluoromethyl-phenyl)-ethyl ester (130 mg, 68.4% yield) as a white solid. LC/MS calcd. for C19H16BrF3N4O2 (m/e) 468/470, obsd. 469/471 (M+H, ES+).

Provenance & Evidence