1,2-Dichloroethane → HCID 42602916, compound

Participants

Reaction Steps

To a DMF solution (9.7 mL) containing 4′-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylic acid (300 mg, 0.97 mmol), HOAt (1.6 mL, 0.97 mmol), DIPEA (0.34 mL, 1.9 mmol), and 2,2,2-trifluoroethanamine (0.23 mL, 2.9 mmol) was added EDC (278 mg, 1.45 mmol). The reaction was stirred at room temperature overnight. EtOAc, NaHCO3 and 3M LiCl were added to the reaction and organics were extracted with EtOAc (3×). The combined organic layers were washed with 3M LiCl (3×) and followed by brine. The final organic layer was dried over Na2SO4, filtered and concentrated. Crude product was taken up in DMF and purified by RP-HPLC. Fractions containing product were combined and sat. NaHCO3 and EtOAc were added. Organics were extracted with EtOAc and washed with brine. Final organic layer was dried over Na2SO4, filtered and concentrated to give a white solid: 1H NMR (CD3OD, 400 MHz) δ 8.07 (s, 1H), 7.93 (s, 1H), 7.90 (s, 1H), 7.55 (d, J=8.2 Hz, 2H), 7.27 (d, J=7.9 Hz, 2H), 5.16 (q, J=7.1 Hz, 1H), 4.09 (q, J=9.2 Hz, 2H), 2.36 (s, 3H); HRMS (ES, M+H) calcd for C18H15F6NO2: 392.1080. found: 392.1079.

Provenance & Evidence