Diisopropylethylamine → HCID 66673010, compound

Participants

Reaction Steps

4-Nitrophenyl chloridocarbonate (268 mg, 1.33 mmol) was added to a mixture of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine (460 mg, 1.33 mmol), diisopropylethylamine (0.695 mL, 4 mmol) in CH2Cl2 (20 mL) at ambient temperature. The mixture was stirred at ambient temperature for 30 min, then concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 give 456 mg (67%) of 4-nitrophenyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.43 (d, 1H, J=2.7 Hz), 8.25 (d, 2H, J=9.2 Hz), 8.14 (d, 2H, J=8.5 Hz), 8.02 (d, 2H, J=8.5 Hz), 7.76 (d, 1H, J=8.7 Hz), 7.37-7.27 (m, 3H), 4.45-4.30 (m, 2H), 3.98 (d, 2H, J=5.1 Hz), 3.16-3.03 (m, 4H), 3.00-2.88 (m, 1H), 2.21-2.06 (m, 1H), 2.04-1.92 (m, 2H), 1.55-1.35 (m, 2H); LRMS (ESI), m/z 512 (M+H).

Provenance & Evidence