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Trityl chloride → 5-Bromo-1-trityl-1H-indazole-3-carboxylic Acid

HRID 34094
ノート
印刷プレビュー

反応式

HRID 34094 の反応式
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[NH:8][N:7]=1)=[O:5])C.[H-].[Na+].[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[N:7]=[C:6]2[C:4]([OH:3])=[O:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12689364ethyl 5-bromo-2H-indazole-3-carboxylate

生成物 1

HCID 230701175-Bromo-1-trityl-1H-indazole-3-carboxylic Acid収率 83.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

2.19 g of 5-bromo-1H-indazole-3-carboxylic acid ethyl ester was dissolved in 40 mL of dimethylformamide, added with 391 mg of 60% sodium hydride (oil-based) and 2.38 g of trityl chloride, and stirred at room temperature for 1 hour. After adding a saturated aqueous ammonium chloride, the reaction solution was extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was evaporated. The resultant residue was dissolved in a solution of 20 mL of ethanol, 20 mL of tetrahydrofuran and 15 mL of 5N sodium hydroxide aqueous, and stirred at 60° C. for 2 hours. After allowing to cool to room temperature, the reaction solution was neutralized by adding 1N hydrochloric acid, extracted with a mixed solvent of ethyl acetate:tetrahydrofuran=1:1, and the resultant organic layer was washed with saturated brine and dried over magnesium sulfate. After evaporated the solvent, the generated crystals were washed with diethyl ether and filtered to afford 3.3 g of the title compound as pale yellow crystals.

後処理

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washthe resultant organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. dissolutionThe resultant residue was dissolved in a solution of 20 mL of ethanol, 20 mL of tetrahydrofuran and 15 mL of 5N sodium hydroxide aqueous
  6. stirringstirred at 60° C. for 2 hours
  7. temperatureto cool to room temperature
  8. additionby adding 1N hydrochloric acid
  9. extractionextracted with a mixed solvent of ethyl acetate
  10. washtetrahydrofuran=1:1, and the resultant organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. customAfter evaporated the solvent
  13. washthe generated crystals were washed with diethyl ether
  14. filtrationfiltered

出典と根拠

ORDレコード
ord-baef361087334cffb56269ad1a6b817d
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07429609B2

反応ノート

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