tert-Butyl 4-(4-((4-((5-fluoro-2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate → tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Participants

Reaction Steps

A suspension of Pd/C 10% (0.100 g) and tert-butyl 4-(4-((4-((5-fluoro-2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A51) (0.158 g, 0.258 mmol) in EtOAc (20 mL) was stirred under a hydrogen atmosphere at room temperature overnight. The resulting mixture was filtered through a Celite plug, washing with EtOAc (100 mL) then the combined organic washings were evaporated in vacuo to yield the title compound A52 as a yellow oil (0.092 g, 58%); 1H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 7.48 (d, J=8.5 Hz, 2H), 7.17-7.10 (m, 3H), 6.91-6.78 (m, 2H), 4.18 (s, 2H), 3.62 (s, 2H), 3.60 (s, 3H), 3.01 (s, 4H), 2.73 (t, J=11.9 Hz, 2H), 2.57 (tt, J=12.0, 3.4 Hz, 1H), 1.75 (d, J=12.8 Hz, 2H), 1.54 (qd, J=12.8, 4.2 Hz, 2H), 1.41 (s, 9H). LCMS-A: rt 6.727/6.998 min; m/z 617 [M+H]+.

Provenance & Evidence