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

HRID 1024391노트

반응식

HRID 1024391 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-680a8283e4f24604a9ef44a96acf541c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722889B2

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