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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
ノート
印刷プレビュー

反応式

HRID 2203418 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c3e726045e7e4ccbb4829a312175cfa4
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365578B2

反応ノート

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