Potassium Carbonate → 1-Methylethyl 4-[({5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)methyl]-1-piperidinecarboxylate

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Reaction Steps

The title compound (80 mg, 49%) was prepared as a white solid from 5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (prepared as in Example 161, Step 2, 98 mg, 0.37 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 131, Step 4, 0.138 g, 0.49 mmol) and K2CO3 (0.102 g, 0.73 mmol) in DMF (4 mL) in a manner similar to Example 152, Step 3. The crude product was purified by chromatography on an ISCO silica gel column using 0 to 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=1.3 Hz), 8.23 (t, 1H, J=7.8 Hz), 7.85-7.70 (m, 2H), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 4H), 3.09 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.85-1.75 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 452 (M+H).

Provenance & Evidence