Potassium Carbonate → 2-[2-Fluoro-4-(methylsulfonyl)phenyl]-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyrazine

Participants

Reaction Steps

The title compound (0.13 g, 49%) was prepared as a white solid from 5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (0.15 g, 0.56 mmol), {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl methanesulfonate (prepared as in Example 100, Steps 1-4, 0.23 g, 0.76 mmol) and K2CO3 (0.16 g, 1.12 mmol) in DMF (6 mL) in a manner similar to Example 152, Step 3. The crude product was purified by chromatography on a silica gel column eluted with 50% EtOAc/hexanes to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.66 (s, 1H), 8.33 (d, 1H, J=1.0 Hz), 8.23 (t, 1H, J=7.8 Hz), 7.82 (dd, 1H, Ja=8.2 Hz, Jb=1.7 Hz), 7.76 (dd, 1H, Ja=10.2 Hz, Jb=1.6 Hz), 4.40-4.30 (m, 2H), 4.29 (d, 2H, J=6.3 Hz), 3.25-3.10 (m, 2H), 3.09 (s, 3H), 2.98 (septet, 1H, J=7.0 Hz), 2.20-2.05 (m, 1H), 2.05-1.90 (m, 2H), 1.60-1.40 (m, 2H), 1.32 (d, 6H, J=6.8 Hz); LRMS (ESI), m/z 476 (M+H).

Provenance & Evidence