Potassium Carbonate → HCID 86638742, compound

Participants

Reaction Steps

Methyl 6-bromo-3-{[(1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinyl)methyl]oxy}-2-pyridinecarboxylate (0.945 g, 86% pure) was prepared as a colorless oil from methyl 6-bromo-3-hydroxy-2-pyridinecarboxylate (0.70 g, 2.78 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 131, Step 4, 1.23 g, 4.16 mmol) and K2CO3 (0.78 g, 5.55 mmol) in DMF (30 mL) in a manner similar to Example 131, Step 5. The crude product was purified by flash chromatography on an ISCO silica gel column using 0 to 45% EtOAc/hexanes. 1H NMR (400 MHz, CDCl3): δ 7.53 (d, 1H, J=8.5 Hz), 7.21 (d, 1H, J=8.8 Hz), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.93 (s, 3H), 3.86 (d, 2H, J=6.3 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.75 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 415/417 (M+H).

Provenance & Evidence