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

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Reaction Steps

The title compound (0.303 g, 61%) was prepared as a white solid from [4-(methylsulfonyl)phenyl]boronic acid (0.28 g, 1.37 mmol), 1-methylethyl 4-{[(5-bromo-2-pyrazinyl)oxy]methyl}-1-piperidinecarboxylate (crude material prepared in Step 2), Pd(PPh3)2Cl2 (82 mg, 0.11 mmol), 2M Na2CO3 (8 mL) and DME (8 mL) in a manner similar to Example 21, Step 3. The crude material was purified by flash chromatography on a silica gel column eluted with 1:20 acetone/CH2Cl2 to 1:10 acetone/CH2Cl2 followed by trituration with hot hexanes containing 1% MeOH to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.56 (s, 1H), 8.31 (s, 1H), 8.12 (d, 2H, J=8.3 Hz), 8.03 (d, 2H, J=8.3 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 4H), 3.09 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 434 (M+H).

Provenance & Evidence