Triethylamine → 5-(2-hydroxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

A mixture of (E)-4,4,4-Trifluoro-3-[4-(2-hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic acid benzyl ester (9.5 g, 19.3 mmol, 1.0 eq), Pd(OAc)2 (433 mg, 1.93 mmol, 0.1 eq), triethylamine (3.1 mL, 23.2 mmol, 1.2 eq), triphenyphosphinc (1.52 g, 5.79 mmol, 0.3 eq) and DMF (20 mL) was heated under refluxing in a 100-mL round bottom flask under nitrogen. The reaction mixture was stirred overnight. After the stirring was stopped, the mixture was partitioned between dichloromethane (100 mL) and water (100 mL) filtered through celite. The organic layer was washed with water (3×100 mL), dried over MgSO4, and concentrated. The crude residue was purified by flash chromatography (SiO2, hexanes-ethyl acetate) to yield 420 mg of the desired indole as pale yellow gel (6.0% yield).

Provenance & Evidence