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4-Toluenesulfonyl chloride → 1H-Pyrrolo[2,3-B]pyridine, 4-chloro-5-fluoro-1-[(4-methylphenyl)sulfonyl]-

HRID 490500
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HRID 490500 반응식
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH:10]=[CH:11][C:3]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

생성물 1

HCID 497588981H-Pyrrolo[2,3-B]pyridine, 4-chloro-5-fluoro-1-[(4-methylphenyl)sulfonyl]-수율 0%

시약·촉매·용매 4

HCID 94433Tetrabutylammonium hydrogen sulfate촉매
HCID 962
Water
용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1.30 g of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, 1.6 g of 4-methylbenzenesulfonyl chloride, 3.40 g of sodium hydroxide dissolved in 16 cm3 of water, and 0.052 g of tetrabutylammonium hydrogen sulfate in 200 cm3 of toluene is stirred for about 24 hours in the region of 20° C. The mixture is diluted with 500 cm3 of ethyl acetate; the organic phase is washed with three times 200 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a column of silica [eluent: dichloromethane]. 1.90 μg of 4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are thus obtained in the form of a powder, the characteristics of which are as follows:

후처리

  1. washthe organic phase is washed with three times 200 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  5. customThe residue is purified by flash chromatography on a column of silica [eluent: dichloromethane]

출처 및 근거

ORD 기록
ord-d74761599469496ea9376a9fea955092
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528147B2

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