Ethyl Acetate → {5-[(4'-Trifluoromethylbiphenyl-2-carbonyl)-amino]indan-2-yl}-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of the title C compound ((5-amino-indan-2-yl)-carbamic acid tert-butyl ester; 12.5 mmol) in methylene chloride (75 mL) is added diisopropylethyl amine (3.3 g, 25 mmol) followed by a 0.5 M solution of the title D compound (4′-trifluoromethyl-2-biphenyl carboxylic acid chloride, 12.6 mmol) in methylene chloride (25.3 mL). After stirring 16 h, the reaction mixture is poured into ethyl acetate and washed with 1N HCl, 8% NaHCO3 solution, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a solid. Recrystallization from toluene gives {5-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]-indan-2-yl}-carbamic acid tert-butyl ester in two crops; mp 198-201° C. MS (ES+), m/z 514 (M+NH+4).

Provenance & Evidence