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4-Vinylpyridine → 3-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine

HRID 2086792
Notes
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Reaction equation

HRID 2086792 reaction equation
I[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:18]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[CH2:19].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+:15]([C:14]1[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2](/[CH:19]=[CH:18]/[C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 75024-VinylpyridineHCID 516892Sodium Bicarbonate2×HCID 227244832-(3-Iodophenylamino)-3-nitropyridine

Product 1

HCID 227240493-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridineYield 39.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalyst
HCID 167845palladium(II) acetateCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(3-iodophenylamino)-3-nitropyridine (3.86 g), 4-vinylpyridine (1.78 g), palladium(II) acetate (80 mg), tetrabutylammonium chloride (3.14 g) and sodium bicarbonate (2.4 g) in N,N-dimethylformamide (20 ml) was stirred at 110° C. for 22 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (chloroform-methanol (50:1)) to give 3-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine (1.41 g) as an orange solid.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-99d04f24b4a64c26b014c367c4055df3
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06727245B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes