Sodium Carbonate → 1-Methylethyl 4-[({2-fluoro-6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

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The title compound (197 mg, 70%) was prepared as a light gray solid from [4-(methylsulfonyl)phenyl]boronic acid (160 mg, 0.75 mmol), 1-methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (235 mg, 0.63 mmol), Pd(PPh3)2Cl2 (45 mg, 0.06 mmol), 2M Na2CO3 (4 mL) and DME (4 mL) in a manner similar to Example 21, Step 3. The crude product was triturated with MeOH to give the title compound as a light gray solid. 1H NMR (400 MHz, CDCl3): δ 8.12 (d, 2H, J=8.3 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.63 (d, 1H, J=8.3 Hz), 7.40-7.30 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 2H), 3.92 (d, 2H, J=6.4 Hz), 3.07 (s, 3H), 2.85-2.70 (m, 2H), 2.15-2.00 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 451 (M+H).

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