3-(Trifluoromethyl)aniline → HCID 21110127, compound

Participants

Reaction Steps

A solution of Example 47A (700 mg, 3.64 mmol), 3-trifluoromethylaniline (646 mg, 4.01 mmol), ethyldiisopropylamine (1036 mg, 8.01 mmol), 1-hydroxy-1H-benzotriazol hydrate (591 mg, 4.37 mmol), and 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (908 mg, 4.74 mmol) in dimethyl formamide (30 ml) is stirred at room temperature overnight (18 h). The solvent is removed in vacuo and the residue is dissolved in 300 ml water/ethyl acetate. The phases are separated and the aqueous phase is extracted three times with ethyl acetate. The organic layers are combined, washed with brine, and the solvent is removed in vacuo. The crude product is purified by flash chromatography over silica gel with cyclohexane/ethyl acetate as eluent. The resulting product is further purified by preparative HPLC (acetonitrile/water 1:9 to 9:1 gradient) to afford a pale yellow solid.

Provenance & Evidence