Tetrafluoroborate → HCID 86712712, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (K5) (0.300 g, 0.656 mmol), PdCl2(PPh3)2 (0.046 g, 0.066 mmol), t-Bu3PH.BF4 (0.019 g, 0.066 mmol), CuI (0.013 g, 0.022 mmol) and methyl 2-(2-ethynyl-5-(trifluoromethyl)phenyl)acetate (A105) (0.191 g, 0.657 mmol) in dry degassed DMF (4 mL) and Et3N (4 mL) was heated at 120° C. for 20 minutes under nitrogen. The volatiles were evaporated under reduced pressure and the residue adsorbed onto silica gel then purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.) to give the title compound A106 as a yellow solid (0.196 g, 45%); 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.62 (s, 1H), 7.60-7.53 (m, 4H), 7.21 (d, J=8.5 Hz, 2H), 4.25 (s, 2H), 3.99 (s, 2H), 3.72 (s, 3H), 2.80 (t, J=11.9 Hz, 2H), 2.64 (m, 1H), 1.82 (d, J=12.8 Hz, 2H), 1.68-1.53 (m, 2H), 1.49 (s, 9H). LCMS-A: rt 7.109 min; m/z 663.3 [M+H]+.

Provenance & Evidence