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

HRID 2203418Notes

Reaction equation

HRID 2203418 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c3e726045e7e4ccbb4829a312175cfa4
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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