[5-(4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester → {5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclopentyl)-ethyl]-3-methyl-phenyl}-propyl)-phenyl]-pyridin-3-yl}-acetic Acid Methyl Ester

HRID 547085Notes

Reaction equation

HRID 547085 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH2:35][CH3:36])([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]4([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:22]([CH3:34])[CH:21]=3)[CH2:18][CH3:19])=[CH:13][CH:12]=2)[CH:10]=1.[H][H]>CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH2:35][CH3:36])([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]4([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:22]([CH3:34])[CH:21]=3)[CH2:18][CH3:19])=[CH:15][CH:16]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 57709096[5-(4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-phenyl)-pyridin-3-yl]-acetic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 57443539{5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclopentyl)-ethyl]-3-methyl-phenyl}-propyl)-phenyl]-pyridin-3-yl}-acetic Acid Methyl EsterYield 79.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% palladium carbon (16 mg) was added to a solution of [5-(4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-phenyl)-pyridin-3-yl]-acetic acid methyl ester (Example 148-(1); 16.4 mg, 0.033 mmol) in methanol (0.2 mL), and the mixture was stirred in a hydrogen atmosphere for 19 hours. The reaction solution was filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the title compound (13.1 mg, 79%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a1ebebe92cfe4c41bb1566bd74a3984e
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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