Trifluoroacetic acid → 5-Fluoro-2-{4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinyl}pyrimidine

Participants

Reaction Steps

The title compound (91 mg, 84%) was prepared as a white solid from 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (prepared as in Example 150, Step 2, 0.11 g, 0.25 mmol) and TFA (0.20 mL) in CH2Cl2 (6 mL) then K2CO3 (0.75 g) and 2-chloro-5-fluoropyrimidine (47 μL, 0.27 mmol) in DMSO (5 mL) in a manner similar to Example 80. The crude material was purified by chromatography on a silica gel column eluted with 1:15 acetone/CH2Cl2 to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.42 (d, 1H, J=2.7 Hz), 8.18 (s, 2H), 8.14 (d, 2H, J=8.3 Hz), 8.02 (d, 2H), J=8.3 Hz), 7.76 (d, 1H, J=8.8 Hz), 7.45-7.35 (m, 1H), 4.80-4.70 (m, 2H), 3.94 (d, 2H, J=6.1 Hz), 3.07 (s, 3H), 3.00-2.85 (m, 2H), 2.10-2.05 (m, 1H), 2.00-1.90 (m, 2H), 1.45-1.30 (m, 2H); LRMS (ESI), m/z 443 (M+H).

Provenance & Evidence