Borane;tetrahydrofuran → 1-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)methyl]-1-piperidinecarboxylate

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Reaction Steps

1-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)methyl]-1-piperidinecarboxylate (195 mg, 49%) was prepared as a yellow solid from 1-methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)carbonyl]-1-piperidinecarboxylate (410 mg, 0.95 mmol), 1M BH3-THF (2.85 mL, 2.85 mmol) and THF (5 mL) in a manner similar to Example 172, Step 3, except that no 1.8M BH3-THF was used. 1H NMR (400 MHz, CDCl3): δ 8.45 (bs, 1H), 7.70 (d, 1H, J=9.0 Hz), 7.64-7.56 (m, 1H), 7.35 (d, 1H, J=9.1 Hz), 7.11 (d, 1H, J=8.2 Hz), 7.01 (d, 1H, J=11.8 Hz), 4.95-4.82 (m, 1H), 4.24-4.08 (m, 2H), 3.08 (d, 2H, J=5.1 Hz), 2.80-2.60 (m, 2H), 2.50 (d, 3H, J=2.1 Hz), 1.85-1.70 (m, 2H), 1.32-1.09 (m, 8H); LRMS (ESI), m/z 418 (M+H).

Provenance & Evidence