Sodium Carbonate → 1,1-Dimethylethyl 4-({[6-(4-bromo-2-fluorophenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate

Participants

Reaction Steps

1,1-Dimethylethyl 4-({[6-(4-bromo-2-fluorophenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (0.23 g, ˜90% purity, 42%) was prepared as a white solid from (4-bromo-2-fluorophenyl)boronic acid (0.30 g, 1.36 mmol), 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.44 g, 1.19 mmol), 2M Na2CO3 (2 mL), and PdCl2(PPh3)2 (85 mg, 0.12 mmol) in DME (4 mL) in a manner similar to Example 21, Step 3. The material was purified by chromatography on a silica gel column eluted with 20% EtOAc/hexanes. 1H NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=2.7 Hz), 7.90-7.85 (m, 1H), 7.72 (d, 1H, J=8.8 Hz), 7.45-7.30 (m, 2H), 7.30-7.25 (m, 1H), 4.25-4.10 (m, 2H), 3.99 (d, 2H, J=6.4 Hz), 2.95-2.80 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.25 (m, 2H); LRMS (ESI), m/z 465/467 (M+H).

Provenance & Evidence