Sodium Carbonate → 1,1-Dimethylethyl 4-{[(2'-fluoro-6'-methyl-2,3'-bipyridin-5-yl)oxy]methyl}-1-piperidine carboxylate

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Reaction Steps

1,1-Dimethylethyl 4-{[(2′-fluoro-6′-methyl-2,3′-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate (0.21 g, 72%) was prepared as an off-white solid from 2-fluoro-6-picoline-3-boronic acid (0.14 g, 0.87 mmol), 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 76, Step 1, 0.27 g, 0.72 mmol), 2M Na2CO3 (2.5 mL) and PdCl2(PPh3)2 (26 mg, 0.04 mmol) DME (8 mL) in a manner similar to Example 21, Step 3. The crude material was purified by chromatography on a silica gel column eluted with 1:10 acetone/CH2Cl2 to give 1,1-dimethylethyl 4-{[(2′-fluoro-6′-methyl-2,3′-bipyridin-5-yl)oxy]methyl}-1-piperidine carboxylate as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.45-8.35 (m, 2H), 7.81 (d, 1H, J=8.0 Hz), 7.30-7.25 (m, 1H), 7.15-7.10 (m, 1H), 4.16 (bs, 2H), 3.88 (d, 2H, J=6.4 Hz), 2.80-2.65 (m, 2H), 2.53 (s, 3H), 2.10-1.90 (m, 1H), 1.90-1.80 (m, 2H), 1.45 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 402 (M+H).

Provenance & Evidence