Tetrabutylammonium Fluoride → 2-Tert-butyl-5-nitro-1H-indole-7-carbonitrile

HRID 1403921ノート

反応式

HRID 1403921 の反応式
[NH2:1][C:2]1[C:9]([C:10]#[C:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][C:3]=1[C:4]#[N:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:12]([C:11]1[NH:1][C:2]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][C:3]=2[C:4]#[N:5])([CH3:15])([CH3:13])[CH3:14]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 591292522-Amino-3-(3,3-dimethylbut-1-ynyl)-5-nitrobenzonitrile

生成物 1

HCID 534211842-Tert-butyl-5-nitro-1H-indole-7-carbonitrile収率 51.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-amino-3-(3,3-dimethylbut-1-ynyl)-5-nitrobenzonitrile (1.7 g, 7.0 mmol) in THF (35 mL) was added TBAF (9.5 g, 28 mmol) at room temperature. The mixture was heated at reflux overnight. The reaction mixture was cooled and the THF was removed under reduced pressure. Water (50 ml) was added to the residue and the mixture was extracted with EtOAc. The organics were dried over Na2SO4 and the solvent was evaporated under vacuum to obtain 0.87 g of crude product 2-tert-butyl-5-nitro-1H-indole-7-carbonitrile which was used directly in the next step without purification.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customthe THF was removed under reduced pressure
  5. additionWater (50 ml) was added to the residue
  6. extractionthe mixture was extracted with EtOAc
  7. dry with materialThe organics were dried over Na2SO4
  8. customthe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-8709fc119514416ab31b1aadf5f2b741
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

読み込み中…