3-(Trifluoromethyl)aniline → HCID 11852874, compound

Participants

Reaction Steps

DIEA (0.15 mL, 0.87 mmol, 4.0 equiv) is added dropwise to a cold (0° C.) mixture of crude (4-imidazo[4,5-c]pyridin-1-yl-phenyl)-acetic acid (55 mg, 0.22 mmol), 3-aminobenzotrifluoride (39 mg, 0.24 mmol, 1.1 equiv), and TBTU (77 mg, 0.24 mmol, 1.1 equiv) in DMF (0.5 mL). The reaction mixture is allowed to warm to rt, stirred for 2 h, diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3, H2O, and brine. The organic phase is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 94:6) to afford the title compound as a white solid: ES-MS: 397.0 [M+H]+; single peak at tR=3.52 min (System 1); Rf=0.18 (CH2Cl2/MeOH, 94:6).

Provenance & Evidence