Methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate → Methyl 13-cyclohexyl-6-(carbomethoxy)-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1394839

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HRID 1394839 반응식
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH2:22])[C:8]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2C=C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[N:9]3[CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH2:22][C:32]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:8]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 1

HCID 58765271Methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate

생성물 1

HCID 69204611Methyl 13-cyclohexyl-6-(carbomethoxy)-5H-indolo[2,1-a][2]benzazepine-10-carboxylate수율 46.8%

시약·촉매·용매 2

HCID 178425456HCID 178425456, 화합물촉매HCID 6344Dichloromethane용매

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온도
45 °C

실험 절차

A mixture of methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate (13, R=methyl), (3.1 g, 6.77 mmol) and Grubbs' 2nd generation catalyst (1.7 g, 1.35 mmol) in methylene chloride (350 mL) were heated at 45° C. for 96 hr. Solvent was removed in vacuo and the residue was chromatographed on silica gel using hexane/ethyl acetate (0-15%) to afford pure title compound as a bright yellow solid (1.36 g). The mixed fractions were combined and concentrated in vacuo and the residue was recrystallized using methanol to afford the title compound (175 mg). Total title compound obtained: 1.805 g, 53%. ESI-MS m/z 430 (MH+).

후처리

  1. customSolvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-c5d35e2251684599bb42077cdefb0200
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348425B2

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