Triethylamine → 2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridine

HRID 1953407Notes

Reaction equation

HRID 1953407 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)=[CH2:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20](/[CH:2]=[CH:1]/[C:3]2[CH:4]=[C:5]([NH:9][C:10]3[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:21]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 232981282-(3-Vinylphenylamino)-3-nitropyridine

Product 1

HCID 227244742-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridineYield 67.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(3-vinylphenylamino)-3-nitropyridine (12.9 g), 3-bromopyridine (12.7 g), palladium(II) acetate (0.24 g), copper(I) iodide (0.10 g), tri-o-tolylphosphine (0.65 g), triethylamine (25 ml) and acetonitrile (150 ml) was stirred under reflux under nitrogen overnight. After removal of the solvents, crude residue was chromatographed on silica gel (450 g, chloroform as eluent) to give 2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridine as a reddish orange crystals (11.5 g).

Workup

  1. temperatureunder reflux under nitrogen overnight
  2. customAfter removal of the solvents, crude residue
  3. customwas chromatographed on silica gel (450 g, chloroform as eluent)

Sources & evidence

ORD record
ord-b49e0b4166e14a6f875f40101f0ba827
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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