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

反応式

HRID 1394839 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178425456HCID 178425456、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-c5d35e2251684599bb42077cdefb0200
出典データセット
uspto-grants-2008_03
特許番号
US07348425B2

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