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

HRID 1953408ノート

反応式

HRID 1953408 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ac9eb382d52d46e39402426b8699a75d
出典データセット
uspto-grants-2000_09
特許番号
US06117875

反応ノート

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