HCID 59177824, compound → HCID 66673312, compound

HRID 423600Notes

Reaction equation

HRID 423600 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH:18]([CH:20]3[CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH2:21]3)[CH3:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.C1COCC1.[Pd]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH3:19])=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 1

HCID 59177824HCID 59177824, compound

Product 1

HCID 66673312HCID 66673312, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(±)-Phenylmethyl 4-[1-({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)ethyl]-1-piperidinecarboxylate (Example 139, 0.37 g, 0.75 mmol) was dissolved in MeOH (10 mL) and THF (5 mL). 10% of Pd/C (40 mg, Degussa type) was added, and the mixture was placed under an atmosphere of hydrogen using a H2 balloon at ambient temperature for 4 h. The mixture was filtered through Celite® and the filtrate was concentrated to give 0.27 g (100%) of (±)-2-[4-(methylsulfonyl)phenyl]-5-{[1-(4-piperidinyl)ethyl]oxy}pyridine as a viscous colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=2.9 Hz), 8.12 (d, 2H, J=8.5 Hz), 8.00 (d, 2H, J=8.3 Hz), 7.72 (d, 1H, J=8.8 Hz), 7.30-7.25 (m, 1H), 4.30-4.20 (m, 1H), 3.20-3.10 (m, 2H), 3.08 (s, 3H), 2.70-2.60 (m, 2H), 1.95-1.65 (m, 3H), 1.45-1.25 (m, 5H); LRMS (ESI), m/z 361 (M+H).

Workup

  1. customat ambient temperature
  2. customfor 4 h
  3. filtrationThe mixture was filtered through Celite®
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5be2ada6b7b943be81151f7829df7d17
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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