Water → 1H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 5-chloro-1-(phenylsulfonyl)-

HRID 509967ノート

反応式

HRID 509967 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[K+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:15]1([S:21]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:10]([CH:11]=[O:12])=[CH:9]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 468564775-chloro-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

生成物 1

HCID 497590321H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 5-chloro-1-(phenylsulfonyl)-収率 36%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To 5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (114, 3.60 g, 19.9 mmol) in 100 mL of dichloromethane, potassium hydroxide (50 mL, 9M aqueous, 0.45 mol), tetrabutylammonium hydrogen sulfate (400 mg, 1.0 mmol) and benzenesulfonyl chloride (11, 2.9 mL, 23.0 mmol) were added. The reaction was stirred at room temperature for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate to provide the desired compound as a white solid (115, 2.3 g).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. washThe resulting material was washed with ethyl acetate

出典と根拠

ORDレコード
ord-9d346830d1ad46c6bb50bca627a4a20a
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

読み込み中…