Trifluoroacetic acid → 1-Methylethyl 4-{[(2'-fluoro-6'-methyl-2,3'-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate

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Reaction Steps

The title compound (0.166 g, 96%) was prepared as a white solid from 1,1-dimethylethyl 4-{[(2′-fluoro-6′-methyl-2,3′-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate (0.18 g, 0.45 mmol) and TFA (0.35 mL) in CH2Cl2 (10 mL) then diisopropylethylamine (2.0 mL) and isopropyl chloroformate (1.0M in toluene, 0.54 mL, 0.54 mmol) in a manner similar to Example 74. The crude material was purified by chromatography on a silica gel column eluted with 1:10 acetone/CH2Cl2 to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.45-8.35 (m, 2H), 7.82 (d, 1H, J=8.6 Hz), 7.30-7.25 (m, 1H), 7.20-7.10 (m, 1H), 4.91 (septet, 1H, J=6.3 Hz), 4.22 (bs, 2H), 3.89 (d, 2H, J=6.4 Hz), 2.85-2.70 (m, 2H), 2.53 (s, 3H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 388 (M+H).

Provenance & Evidence