Sodium Carbonate → HCID 24993714, compound

Participants

Reaction Steps

The title compound (0.785 g, 82%) was prepared as a light yellow solid from [4-(methylsulfonyl)phenyl]boronic acid (0.48 g, 2.36 mmol), methyl 6-bromo-3-{[(1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinyl)methyl]oxy}-2-pyridinecarboxylate (0.945 g, 86% pure), Pd(PPh3)2Cl2 (0.14 g, 0.20 mmol), 2M Na2CO3 (6 mL) and DME (20 mL) in a manner similar to Example 21, Step 3. The crude material was purified by chromatography on a silica gel column eluted with 1:10 acetone/CH2Cl2 followed by trituration with hot hexanes containing 1% of MeOH to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.15 (d, 2H, J=8.3 Hz), 8.01 (d, 2H, J=8.5 Hz), 7.86 (d, 1H, J=8.8 Hz), 7.41 (d, 1H, J=8.8 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.99 (s, 3H), 3.94 (d, 2H, J=6.3 Hz), 3.06 (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 491 (M+H).

Provenance & Evidence