Ethyl Acetate → 2-(3-(3-Fluorophenyl)-1H-5-indazolyl]acetonitrile

HRID 503120ノート

反応式

HRID 503120 の反応式
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OC(C)(C)C)=O)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1.[C-:26]#[N:27].[Na+].C(OCC)(=O)C>CS(C)=O>[F:25][C:21]1[CH:20]=[C:19]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][C:26]#[N:27])[CH:4]=3)[NH:8][N:7]=2)[CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 222606161h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

生成物 1

HCID 222606222-(3-(3-Fluorophenyl)-1H-5-indazolyl]acetonitrile収率 8.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 1.0 g of tert-butyl 5-(chloromethyl)-3-(3-fluorophenyl)-1H-1-indazolecarboxylate in 5 ml dimethyl sulfoxide was added 204 mg of sodium cyanide, and the mixture was stirred at room temperature for 50 minutes. To the reaction mixture was added 50 ml of ethyl acetate, and after washing with water, the aqueous layer was re-extracted with diethyl ether. The collected organic layer was sequentially washed with water (×2) and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=1:9), and suspended in diethyl ether-diisopropyl ether, to give 62 mg of the title compound as yellow crystals.

後処理

  1. washafter washing with water
  2. extractionthe aqueous layer was re-extracted with diethyl ether
  3. washThe collected organic layer was sequentially washed with water (×2) and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:toluene=1:9)

出典と根拠

ORDレコード
ord-140b002579f946f7a639c47367376847
出典データセット
uspto-grants-2010_08
特許番号
US07776890B2

反応ノート

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