1-(2-Ethynylphenyl)cyclopropanecarboxamide → 1-(2-((2-((6-Methoxypyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2-ethynylphenyl)cyclopropanecarboxamide K6 (0.120 g, 0.648 mmol), 4-chloro-N-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-amine A68 (0.197 g, 0.648 mmol), CuI (0.012 g, 0.065 mmol), t-Bu3PHBF4 (0.019 g, 0.065 mmol) and PdCl2(PPh3)2 (0.023 g, 0.032 mmol) in DMF (3 mL) was bubbled with N2 for 5 minutes. Et3N (1 mL) was added and the reaction mixture was stirred in the microwave at 120° C. for 15 minutes. The volatiles were removed in vacuo and the black residue was adsorbed onto silica. Purification by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) gave the title compound A73 as a yellow solid (0.229 g, 78%). LCMS-D: rt 3.47 min; m/z 454 [M+H]+.

Provenance & Evidence