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

HRID 2251850Notes

Reaction equation

HRID 2251850 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH2:7]2.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)(Cl)Cl.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH2:7][C:6]3[C:10](=[C:2]([CH:23]=[CH:22][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[CH:3]=[CH:4][CH:5]=3)[C:9]2=[O:11])=[CH:13][CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 690317107-Bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

7-Bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one (0.14 g), 4-vinylpyridine (0.55 mL), Pd(OAc)2 (1.2 mg), tri-o-tolylphosphine (27.3 mg), and 2 mL of Et3N were added into a microwave reaction tube and subjected to 120° C., 10 min of microwave (2×). H2O and CHCl3 were added and the layers were separated. The aqueous phase was extracted with CHCl3 (3×). The combined organic phases were washed with H2O, dried over Na2SO4, filtered, then evaporated in vacuo to yield a light brown residue as crude product. The crude was purified by silica gel chromatography (25 g, 10-50% EtOAc/hexanes) to afford 2-(4-t-butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one as an off-white solid:

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with CHCl3 (3×)
  3. washThe combined organic phases were washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a light brown residue as crude product
  8. customThe crude was purified by silica gel chromatography (25 g, 10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-96eb40bc7dbe449584a240075a13b75c
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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