4-Toluenesulfonyl chloride → 4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine

HRID 632739노트

반응식

HRID 632739 반응식
[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[H-].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[N:10]([S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[CH:11]=[CH:12][C:3]=12

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 118064014-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine

생성물 1

HCID 896575464-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine (7.42 g, 32.7 mmol) in dimethylformamide (235 mL) was stirred at room temperature. To this solution was added sodium hydride (1.18 g, 1.96 g of 60% dispersion in oil, 49.0 mmol), and the reaction mixture was stirred for 10 minutes. P-toluenesulfonyl chloride (9.35 g, 49.0 mmol) was then added portion-wise, and the mixture was stirred at room temperature under nitrogen for 16 hours. The reaction mixture was quenched carefully with water and the resulting beige solid collected by vacuum filtration on a Buchner funnel, and washed with water. The solid was collected and dried in a vacuum oven at 50° C. to provide 12.4 g (100%) of 4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine.

후처리

  1. stirringthe mixture was stirred at room temperature under nitrogen for 16 hours
  2. customThe reaction mixture was quenched carefully with water
  3. filtrationthe resulting beige solid collected by vacuum filtration on a Buchner funnel
  4. washwashed with water
  5. customThe solid was collected
  6. customdried in a vacuum oven at 50° C.

출처 및 근거

ORD 기록
ord-35959e81d8fa49a59b25c2eba5b2f93d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321765B2

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