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

Participants

Reaction Steps

1,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (6.87 g, 88%) was prepared as a gray solid from 1,1-dimethylethyl 4-{[(6-chloro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 73, Step 1, 5.73 g, 17.5 mmol), [4-(methylsulfonyl)phenyl]boronic acid (3.85 g, 17.53 mmol), Pd(PPh3)4 (10.13 g, 8.76 mmol), 2M Na2CO3 (26 mL) in DME (170 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CDCl3): δ 8.40 (d, 1H, J=2.9 Hz), 8.15-8.12 (m, 2H), 8.02-7.99 (m, 2H), 7.73 (d, 1H, J=8.7 Hz), 7.28 (dd, 1H, Ja=8.7 Hz, Jb=3.0 Hz), 4.19 (bs, 2H), 3.91 (d, 2H, J=6.4 Hz), 3.08 (s, 3H), 2.81-2.71 (m, 2H), 2.07-1.96 (m, 1H), 1.87-1.82 (m, 2H), 1.47 (s, 9H), 1.36-1.24 (m, 2H); LRMS (APCI), m/z 447 (M+H).

Provenance & Evidence