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

HRID 1953407
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HRID 1953407 반응식
[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
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참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 80271
Tri-o-tolylphosphine
촉매
HCID 167845palladium(II) acetate촉매
HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b49e0b4166e14a6f875f40101f0ba827
출처 데이터셋
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06117875

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