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 1394839Notes

Reaction equation

[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

Participants

Conditions

Temperature: 45 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-c5d35e2251684599bb42077cdefb0200
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348425B2

Reaction notes

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