Dimethylformamide → HCID 86712674, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (K5) (0.200 g, 0.438 mmol), PdCl2(PPh3)2 (0.031 g, 0.044 mmol), t-Bu3PH.BF4 (0.013 mg, 0.044 mmol), CuI (0.008 g, 0.044 mmol) and methyl 2-(2-ethynyl-4-(trifluoromethyl)phenyl)acetate (A59) (0.212 g, 0.875 mmol) in anhydrous, degassed DMF (6 mL) and Et3N (6 mL) was heated at 120° C. for 20 minutes under nitrogen. The volatiles were evaporated under reduced pressure then the residue adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A60 as a brown solid (0.176 g, 61%); 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.93 (d, J=0.8 Hz, 1H), 7.67 (dd, J=8.2, 1.3 Hz, 1H), 7.56 (d, J=8.5 Hz, 2H), 7.51-7.49 (m, 2H), 7.23 (d, J=8.5 Hz, 2H), 4.36-4.18 (m, 2H), 4.01 (s, 2H), 3.72 (s, 3H), 2.91-2.74 (m, 2H), 2.72-2.58 (m, 1H), 1.83 (d, J=12.6 Hz, 2H), 1.64-1.56 (m, 2H), 1.50 (s, 9H). LCMS-A: rt 7.227 min; m/z 661 [M−H]−.

Provenance & Evidence