Diisopropylamine → 3-Cyano-6,7-dimethoxy-4-[6chloro-4-(3-methoxyprop-1-ynyl)-2,3-methylene dioxyanilino]quinoline

HRID 347424노트

반응식

HRID 347424 반응식
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])=[C:6]2[O:25][CH2:26][O:27][C:5]2=[C:4](I)[CH:3]=1.[CH2:29]([O:32][CH3:33])[C:30]#[CH:31].C(NC(C)C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:23]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([C:31]#[C:30][CH2:29][O:32][CH3:33])=[C:5]3[O:27][CH2:26][O:25][C:6]=13)=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)#[N:24]

참가 물질

6

반응물 3

HCID 7912DiisopropylamineHCID 693933-MethoxypropyneHCID 179805104-(6-Chloro-4-iodo-2,3-methylenedioxyan ilino)-3-cyano-6,7-dimethoxyquinoline

생성물 1

HCID 104339863-Cyano-6,7-dimethoxy-4-[6chloro-4-(3-methoxyprop-1-ynyl)-2,3-methylene dioxyanilino]quinoline

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-(6-chloro-4-iodo-2,3-methylenedioxyanilino)-3-cyano-6,7-dimethoxyquinoline (0.25 g), methyl 2-propynyl ether (0.09 ml), N,N-diisopropylamine (0.154 ml), bis(triphenylphosphine)palladium(II) dichloride (0.069 g), cuprous iodide (0.028 g) and ethyl acetate (10 ml) was stirred and heated to reflux for 12 hours. The reaction mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of hexane and ethyl acetate as eluent. There was thus obtained the title compound as an oil (0.138 g); NMR Spectrum: (DMSOd6) 3.42 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 4.38 (s, 2H), 6.17 (s, 2H), 7.13 (s, 1H), 7.36 (s, 1H), 7.92 (s, 1H), 8.39 (s, 1H), 9.42 (br s, 1H); Mass Spectrum: M+H+ 452.

후처리

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customevaporated
  6. customthe residue was purified by column chromatography on silica using
  7. temperatureincreasingly polar mixtures of hexane and ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-ef3b890825fd4f318b4f1a3c911c3a11
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173135B2

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