Water → 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-methoxy-1-(phenylsulfonyl)-

HRID 509928ノート

反応式

HRID 509928 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[C:15]1([S:21]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292443-Iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 591287071H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-methoxy-1-(phenylsulfonyl)-収率 70.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine (15, 4.30 g, 15.7 mmol) in 53.6 mL of N,N-dimethylformamide under nitrogen, sodium hydride (0.690 g, 60% in mineral oil, 17.2 mmol) was added. After 10 minutes, benzenesulfonyl chloride (11, 2.20 mL, 17.2 mmol) was added and the reaction was cooled in a water bath. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate purified by silica gel column chromatography, eluting with 30-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (16, 4.60 g).

後処理

  1. temperaturethe reaction was cooled in a water bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate purified by silica gel column chromatography
  6. washeluting with 30-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-5d4e50848f19428783ee250d56b8a1cd
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

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