2-(4-t-Butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one → 2-(4-t-Butyl-phenyl)-7-(2-pyridin-4-yl-ethyl)-2,3-dihydro-isoindol-1-one

HRID 2251851Notes

Reaction equation

HRID 2251851 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:19][C:18]3[C:13](=[C:14]([CH:20]=[CH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:19][C:18]3[C:13](=[C:14]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=4)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 690310652-(4-t-Butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one

Product 1

HCID 113032132-(4-t-Butyl-phenyl)-7-(2-pyridin-4-yl-ethyl)-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-t-Butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one (92 mg, Example 67) and 10% Pd/C (22 mg) were weighed into a flask. EtOH (7 mL) was added and the mixture was stirred under balloon pressure of H2 at RT for 8.5 h. Catalyst was removed by filtration and the filtrate was concentrated to give a white solid as crude product. The crude was purified by silica gel chromatography (25 g, 10-50% EtOAc/hexanes) to afford 2-(4-t-butyl-phenyl)-7-(2-pyridin-4-yl-ethyl)-2,3-dihydro-isoindol-1-one as a white solid. MS: (ES+) 371(M+H). Calc'd. for C25H26N2O—370.49.

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto give a white solid as crude product
  4. customThe crude was purified by silica gel chromatography (25 g, 10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-37f78d8f4a3e4079b56b69917bdac85b
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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