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

HRID 1953408노트

반응식

HRID 1953408 반응식
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

참가 물질

7

반응물 3

HCID 75024-VinylpyridineHCID 516892Sodium Bicarbonate2회HCID 232980802-[3-[(E)-2-(5-bromopyridin-3-yl)vinyl]phenylamino]-3-nitropyridine

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac9eb382d52d46e39402426b8699a75d
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06117875

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