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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl 8-(2-bromo-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate

HRID 595100
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HRID 595100 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3=[CH:12][CH:13]=[N:14][N:7]3[CH:6]=[CH:5][C:4]=2[C:3]=1[C:15]([O:17][CH3:18])=[O:16].[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1.C(Cl)Cl>[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3=[CH:12][CH:13]=[N:14][N:7]3[CH:6]=[CH:5][C:4]=2[C:3]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:29])=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86712816Methyl 8-aminopyrazolo[5,1-a]isoquinoline-7-carboxylate2회

생성물 1

HCID 70984312Methyl 8-(2-bromo-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate수율 37.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane
용매

실험 절차

A mixture of methyl 8-aminopyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 6, 0.140 g) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.190 g) in pyridine (4 mL) and DCM (3 mL) was stirred at room temperature overnight. The resultant mixture was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%. The resultant glass was triturated with ether to give methyl 8-(2-bromo-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate (0.103 g) as an off-white solid.

후처리

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%
  4. customThe resultant glass was triturated with ether

출처 및 근거

ORD 기록
ord-aab4e70aedc04eb988b122b8dc9115f0
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242997B2

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