Sodium Carbonate → HCID 66672679, compound

Participants

Reaction Steps

1-Methylethyl 4-({[6-(4-{[2-(methoxy)ethyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (0.19 g, 61%) was prepared as a light yellow solid from (4-{[2-(methoxy)ethyl]thio}phenyl)boronic acid (0.23 g, 75% pure, 0.80 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (from Step 1, 0.25 g, 0.70 mmol), 2M Na2CO3 (2 mL) and PdCl2(PPh3)2 (50 mg, 0.07 mmol) in DME (3 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.7 Hz), 7.86 (d, 2H, J=8.3 Hz), 7.64 (d, 1H, J=8.7 Hz), 7.42 (d, 2H, J=8.3 Hz), 7.30-7.25 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.23 (bs, 2H), 3.89 (d, 2H, J=6.3 Hz), 3.59 (t, 2H, J=6.7 Hz), 3.37 (s, 3H), 3.15 (t, 2H, J=6.8 Hz), 2.95-2.80 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 445 (M+H).

Provenance & Evidence