Triethylamine → 3-{3-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-pyridin-4-yl}-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[4-(5-chloro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (160 mg, 338 μmol, example 82) in MeOH (1.2 mL) and EtOAc (1.2 mL) was added PdCl2(dppf)-CH2Cl2 complex (31.8 mg, 38.9 μmol, CAS RN 851232-71-8) and NEt3 (51.4 mg, 70.7 μL, 508 μmol). The reaction mixture was stirred at 150° C. at 70 bar under CO atmosphere for 24 hours. The reaction mixture was treated with silica gel and directly 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). Light yellow oil (39 mg, 23%). MS (ESI): m/z=497.129 [M+H]+.

Provenance & Evidence