Triethylamine → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide (100 mg, 213 μmol, example 74) in MeOH (1.5 mL) and EtOAc (1.5 mL) was added PdCl2(dppf)-CH2Cl2 complex (20.0 mg, 24.5 μmol, CAS RN 851232-71-8) and NEt3 (32.3 mg, 44.5 μl, 319 μmol). The reaction mixture was stirred at 100° C. at 80 bar under CO atmosphere for 18 hours. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (93 mg, 97%). MS (TurboSpray): m/z=449.088 [M+H]+.

Provenance & Evidence