4-Vinylpyridine → 2-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]-3-nitropyridine

HRID 1953408Notes

Reaction equation

HRID 1953408 reaction equation
Br[C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([NH:16][C:17]3[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[N:6][CH:7]=1.[CH:26]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)=[CH2:27].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:31]1[CH:32]=[CH:33][C:28](/[CH:26]=[CH:27]/[C:2]2[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]3[CH:11]=[C:12]([NH:16][C:17]4[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH:13]=[CH:14][CH:15]=3)[CH:5]=[N:6][CH:7]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 75024-VinylpyridineHCID 516892Sodium Bicarbonate2×HCID 232980802-[3-[(E)-2-(5-bromopyridin-3-yl)vinyl]phenylamino]-3-nitropyridine

Product 1

HCID 232981352-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]-3-nitropyridineYield 40.8%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[3-[(E)-2-(5-bromopyridin-3-yl)vinyl]phenylamino]-3-nitropyridine (800 mg), 4-vinylpyridine (233 mg), palladium(II) acetate (27 mg), tetra-n-butylammonium chloride (616 mg) and sodium bicarbonate (432 mg) in N,N-dimethylformamide (4 ml) was stirred at 120pbC. for 4 hours. The mixture was poured into sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 2-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]-3-nitropyridine (346 mg).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic solution was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-ac9eb382d52d46e39402426b8699a75d
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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