4-Toluenesulfonyl chloride → 3-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1024391ノート

反応式

HRID 1024391 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[Li]CCCC.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:3]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

生成物 1

HCID 216691553-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3 g (0.015 mol) of 2 in 20 mL of anhydrous THF was cooled to −78° C. and n-BuLi 2.5 M in hexanes (6.7 mL, 0.167 mol) was added dropwise. After 15 minutes of stirring, tosyl chloride in 5 mL of THF was added dropwise. The cooling bath was removed and the reaction mixture stirred at rt for 1 h. Extracted with ether and the organic phase washed with brine, dried with magnesium sulfate and concentrated in vacuo to give a white solid that was passed through a pad of silica (70% EtOAc; 30% Hexanes) to give 4.65 g (84%) of 3. 1H NMR CDCl3 8.4 (s, 1H), 8.1 (d, 2H), 7.8 (s, 2H), 7.2 (m, 3H), 2.3 (s, 3H).

後処理

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture stirred at rt for 1 h
  3. extractionExtracted with ether
  4. washthe organic phase washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid

出典と根拠

ORDレコード
ord-680a8283e4f24604a9ef44a96acf541c
出典データセット
uspto-grants-2014_05
特許番号
US08722889B2

反応ノート

読み込み中…