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Potassium Carbonate → 4-Chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate

HRID 2203418
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HRID 2203418 반응식
ClC1C=CC([C:8]2[C:9]([F:20])=[C:10]([S:16]([O-:19])(=[O:18])=O)[CH:11]=[C:12]([F:15])[C:13]=2F)=CC=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([C:35]2[N:40]3[CH:41]=[CH:42][N:43]=[C:39]3[CH:38]=[CH:37][CH:36]=2)[CH:29]=1>CS(C)=O.C(OCC)(=O)C.O>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:13]2[C:12]([F:15])=[CH:11][C:10]([S:16]([O:24][C:21]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)(=[O:18])=[O:19])=[C:9]([F:20])[CH:8]=2)=[C:30]([C:35]2[N:40]3[CH:41]=[CH:42][N:43]=[C:39]3[CH:38]=[CH:37][CH:36]=2)[CH:29]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 1317357874-Chlorophenyl-2,4,5-trifluorobenzenesulfonateHCID 1365088014-Chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol

생성물 1

HCID 895441914-Chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate수율 66%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide
용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of 4-chlorophenyl-2,4,5-trifluorobenzenesulfonate (1.64 g, 5.10 mmol) and potassium carbonate (2.11 g, 15.3 mmol) in dimethylsulfoxide (15 mL) at ambient temperature was added 4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol (1.25 g, 5.10 mmol). The mixture was stirred at ambient temperature for 3 h and diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-50% gradient of ethyl acetate in dichloromethane to afford 4-chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate as a colorless foam in 66% yield (1.84 g): 1H NMR (300 MHz, DMSO-d6) δ7.92-7.40 (m, 10 H), 7.27 (dd, J=7.5, 7.5 Hz, 1H), 7.11-6.90 (m, 3H); MS (ES+) m/z 546.8 (M+1), 548.8 (M+1).

후처리

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with a 20-50% gradient of ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-c3e726045e7e4ccbb4829a312175cfa4
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365578B2

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