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Water → HCID 68488403、化合物

HRID 21227
ノート
印刷プレビュー

反応式

HRID 21227 の反応式
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39])(=O)=O.O.[C:43](#[N:45])C>[C-]#N.[Zn+2].[C-]#N>[C:43]([C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39])#[N:45]
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

5

反応物 3

HCID 962WaterHCID 6342AcetonitrileHCID 866282864-Trifluoromethanesulfonyloxy-7-(1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

生成物 1

HCID 68488403HCID 68488403、化合物収率 83%

試薬・触媒・溶媒 1

HCID 11186Zinc cyanide (Zn(CN)2)触媒

反応条件

温度
90 °C

実験手順

4-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (300 mg, 0.505 mmol) was dissolved in acetonitrile (15 mL), and the solution was added with zinc cyanide (178 mg, 1.52 mmol) and [bis(diphenylphosphino)ferrocene]dichloropalladium (33 mg, 0.0404 mmol), followed by stirring at 90° C. for 17 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=8/1) to obtain 4-cyano-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (198 mg, yield 83%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=8/1)

出典と根拠

ORDレコード
ord-38f1ff82bedd4bc08a87e3d93a7eb5ce
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07745641B2

反応ノート

読み込み中…

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