N-Iodosuccinimide → HCID 178455023、化合物

HRID 41512

反応式

HRID 41512 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I:18]N1C(=O)CCC1=O>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:18])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

生成物 1

HCID 178455023HCID 178455023、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Cool a solution of 5-(tert-butyldimethylsilyloxy)-1H-indazole (300.00 g, 1.21 mol) in DCM (4.00 L) to 10° C. in a 10 L jacketed reactor vessel. To the resulting solution add N-iodosuccinimide (298.89 g, 1.33 mol) in portions over 0.5 hours. Stir the mixture at RT for 3 hours to give complete conversion as indicated by liquid chromatography mass spectrometry (LC-MS) and thin layer chromatography (TLC). Cool the mixture to 10° C. and quench with water (2.5 L). Transfer the mixture to a separatory funnel and extract the aqueous layer into DCM (2.5 L). Wash the combined organic extracts with a 10% aqueous sodium thiosulfate solution (5 L) and brine. Dry the organic solution over magnesium sulfate, filter and concentrate in vacuo to afford the title compound as an orange solid. Yield: 388 g (90%). MS (ES) m/z 375 [M+1]+.

後処理

  1. customto give complete conversion
  2. temperatureCool the mixture to 10° C.
  3. customquench with water (2.5 L)
  4. extractionTransfer the mixture to a separatory funnel and extract the aqueous layer into DCM (2.5 L)
  5. washWash the combined organic extracts with a 10% aqueous sodium thiosulfate solution (5 L) and brine
  6. dry with materialDry the organic solution over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-23b85a6c0d2c494a8c727ff6dcf8039d
出典データセット
uspto-grants-2013_09
特許番号
US08530665B2

関連ノート

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