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Iodoacetamide → 2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide

HRID 244411
ノート
印刷プレビュー

反応式

HRID 244411 の反応式
[F:1][C:2]([F:30])([F:29])[C:3]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[N:9]=[CH:8]2)[OH:4].[OH-].[K+].I[CH2:34][C:35]([NH2:37])=[O:36]>CN(C=O)C>[F:30][C:2]([F:1])([F:29])[C:3]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH2:34][C:35]([NH2:37])=[O:36])[CH:21]=1)([OH:4])[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[N:9]=[CH:8]2
参加物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 3727IodoacetamideHCID 14797Potassium HydroxideHCID 249609182,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol

生成物 1

HCID 249609192-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide収率 39.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a chilled (0° C.) solution of 45 mg (0.11 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol in 5 mL of DMF was added 13 mg (0.17 mmol) of powder KOH followed by 31 mg (0.17 mmol) of iodoacetamide. The mixture was stirred over night at room temperature, poured onto ice water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were dried over sodium sulfate, adsorbed on to silica gel and purified by Combiflash chromatography using EtOAc/hexanes (0-80% gradient, product eluted at 40% EtOAc) to provide a colorless film. The material from the column was crystallized from EtOAc-hexanes to afford 20 mg (39%) of the title compound as a colorless powder.

後処理

  1. additionpoured onto ice water
  2. extractionextracted with three 20 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. custompurified by Combiflash chromatography
  5. customto provide a colorless film
  6. customThe material from the column was crystallized from EtOAc-hexanes

出典と根拠

ORDレコード
ord-fe24cff42f9041a6be5df12104d66299
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658637B2

反応ノート

読み込み中…

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