1-(5-Chloro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 4'-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-phenyl]-6-chloro-2'-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 658921ノート

反応式

HRID 658921 の反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][C:27]([CH2:34][CH3:35])([C:30]([O:32][CH3:33])=[O:31])[CH2:28][CH3:29])/[C:9]1=[O:36])=O)(C)(C)C.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:53])=[C:42]([CH:44]=[N:45][C:46]([O:48][Si](C)(C)C)=[CH2:47])[CH:43]=1>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:36])[C:10]3([CH:18]([C:19]4[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=4[O:26][C:27]([CH2:28][CH3:29])([C:30]([O:32][CH3:33])=[O:31])[CH2:34][CH3:35])[CH2:47][C:46](=[O:48])[NH:45][CH:44]3[C:42]3[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]=3[CH3:53])[C:11]2=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 702039431-(5-Chloro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86632089Z-3-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 722961904'-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-phenyl]-6-chloro-2'-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione収率 19.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A mixture of E/Z-3-[5-chloro-2-(1-methoxycarbonyl-1-ethyl-propoxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.63 g, 4.9 mmol) prepared in Example 16 and 1-(5-chloro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (20 mmol) in toluene (20 mL) was heated at 60° C. for 3 h, and concentrated in vacuo. To the residue was added DCM (20 mL) and TFA (10 mL), and the resulting solution was stirred at room temperature for 3 h, then concentrated, partitioned between ethyl acetate and diluted aqueous NaOH solution. The organic layer was separated, washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by flash column chromatography to give the title compound as white solid (600 mg).

後処理

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added DCM (20 mL) and TFA (10 mL)
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and diluted aqueous NaOH solution
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-74abb2359fad4efba4031f2f9fe66766
出典データセット
uspto-grants-2011_12
特許番号
US08076482B2

反応ノート

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