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Potassium Carbonate → (1R,2S)-2-(4-chlorophenyl)-1'-(1-trityl-1 H-imidazol-4-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805387
ノート
印刷プレビュー

反応式

HRID 1805387 の反応式
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C@@H:33]2[C@:35]3([C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[NH:37][C:36]3=[O:44])[CH2:34]2)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)CCN>C(#N)C.[Cu]I>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]2[C@@:35]3([C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]([C:2]4[N:3]=[CH:4][N:5]([C:7]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)([C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:6]=4)[C:36]3=[O:44])[CH2:34]2)=[CH:31][CH:32]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 6182524-Iodo-1-tritylimidazoleHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

生成物 1

HCID 58305304(1R,2S)-2-(4-chlorophenyl)-1'-(1-trityl-1 H-imidazol-4-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

4-iodo-1-trityl-1H-imidazole (210 mg, 0.48 mmol) was added to a suspension of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (107 mg, 0.4 mmol) in acetonitrile (2 mL) under a nitrogen atmosphere. A steady stream of nitrogen was bubbled through the suspension as it was heated to 40° C. over 15 minutes. Potassium carbonate (110 mg, 0.8 mmol), copper (I) iodide (12 mg, 15 mol %), and N,N-dimethylethylenediamine (0.12 mmol, 30 mol %) were added and the reaction mixture was heated to 80° C. for 21 hours under nitrogen atmosphere. The mixture was cooled to room temperature, filtrated, and concentrated to give the title product. The residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether) to give racemic trans-2-(4-chlorophenyl)-1′-(1H-imidazol-4-trityl) spiro[cyclopropane-1,3′-indolin]-2′-one (157 mg, 68%). LC/MS m/e calcd. for C38H28ClN3O: 577, observed (M+H)+: 578.3.

後処理

  1. customA steady stream of nitrogen was bubbled through the suspension as it
  2. temperaturethe reaction mixture was heated to 80° C. for 21 hours under nitrogen atmosphere
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltrated
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-5f60c6cb85d84004919d393f41825ea0
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354443B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート