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

HRID 2230968Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-06c006dc4ee54cf887e1f6ee50d1cd48
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426345B1

Reaction notes

Loading…