Sodium Carbonate → 1,1-Dimethylethyl 4-({[6-(4-{[3-(methoxy)propyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate

Participants

Reaction Steps

1,1-Dimethylethyl 4-({[6-(4-{[3-(methoxy)propyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (0.384 g, 86%) was prepared as a yellow solid from (4-{[3-(methoxy)propyl]thio}phenyl)boronic acid (0.27 g, 1.13 mmol), 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 76, Step 1, 0.35 g, 0.94 mmol), 2M Na2CO3 (5 mL) and PdCl2(PPh3)2 (68 mg, 0.09 mmol) in DME (6 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.2 Hz), 7.84 (d, 2H, J=8.3 Hz), 7.63 (d, 1H, J=8.8 Hz), 7.39 (d, 2H, J=8.3 Hz), 7.25-7.20 (m, 1H), 4.17 (bs, 2H), 3.88 (d, 2H, J=6.3 Hz), 3.48 (t, 2H, J=6.0 Hz), 3.32 (s, 3H), 3.04 (t, 2H, J=7.2 Hz), 2.85-2.70 (m, 2H), 2.05-1.80 (m, 5H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 473 (M+H).

Provenance & Evidence