4-[5-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2-cyclopentyl-6-methoxy-pyridine → 4-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenol

HRID 245117Notes

Reaction equation

HRID 245117 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:22]=3)[N:17]=2)=[CH:11][C:10]=1[CH2:34][CH3:35])C1C=CC=CC=1>C1COCC1.CO.[Pd]>[CH:29]1([C:23]2[CH:22]=[C:21]([C:18]3[N:17]=[C:16]([C:12]4[CH:13]=[C:14]([CH3:15])[C:9]([OH:8])=[C:10]([CH2:34][CH3:35])[CH:11]=4)[O:20][N:19]=3)[CH:26]=[C:25]([O:27][CH3:28])[N:24]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 1

HCID 674912534-[5-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2-cyclopentyl-6-methoxy-pyridine

Product 1

HCID 1363910174-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenolYield 79.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (150 mg, 10% Pd) is added to a solution of 4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2-cyclopentyl-6-methoxy-pyridine (1040 mg, 2.22 mmol) in THF (20 mL) and methanol (20 mL). The mixture is stirred under 1 bar of H2 at rt for 24 h. The catalyst is removed by filtration and the filtrate is concentrated and dried to give 4-[3-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenol (672 mg) as an off-white solid; LC-MS**: tR=0.97 min, [M+H]+=380.27.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customdried

Sources & evidence

ORD record
ord-2e261479cf454cc3b56f0fd715a5cc5b
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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