Benzenesulfonyl chloride → HCID 45270766、化合物

HRID 273314

反応式

HRID 273314 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC.CS(C)=O>[C:12]1([S:18]([N:3]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 92264-AzaindoleHCID 24758Sodium hydride

生成物 1

HCID 45270766HCID 45270766、化合物収率 83%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8058Hexane溶媒

実験手順

Sodium hydride (60% in mineral oil, 203 mg, 5.08 mmol) was washed twice with hexane, and the residue suspended in DMSO (5 ml). 1H-Pyrrolo[3,2-b]pyridine (500 mg, 4.24 mmol) was added and the reaction stirred for 15 minutes. Benzenesulphonyl chloride (749 mg, 4.42 mmol) was added rapidly and the reaction stirred for 0.5 h. After quenching with water the product was extracted into EtOAc, dried (Na2SO4) and concentrated in vacuo. Chromatography (EtOAc, silica) yielded the title compound as a white crystalline solid (903 mg, 83%). δH (d6-DMSO) 8.48 (1H, dd, J 0.8, 3.8 Hz), 8.31 (1H, m), 8.15 (1H, d, J 3.8 Hz), 8.04 (2H, m), 7.72 (1H, m,), 7.61 (2H, m,), 7.36 (1H, dd, J 4.7, 8.4 Hz), 6.98 (1H, dd, J 0.8, 3.8 Hz). LCMS (ES+) RT 3.056 minutes, 259 (M+H)+.

後処理

  1. stirringthe reaction stirred for 0.5 h
  2. customAfter quenching with water the product
  3. extractionwas extracted into EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7afaea33b9224b6aba0d9aaf3a6888a7
出典データセット
uspto-grants-2008_11
特許番号
US07456286B2

関連ノート

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