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

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

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+).

Aufarbeitung

customSolvent was removed in vacuo
customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-c5d35e2251684599bb42077cdefb0200
Quelldatensatz: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07348425B2

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