Cesium carbonate → (2,4-Difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester

HRID 1889171Notes

Reaction equation

HRID 1889171 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:18][C:19](=[O:37])[CH:20](Br)[C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH3:17]>C(#N)C.O>[CH2:16]([O:18][C:19](=[O:37])[CH:20]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:21]1[CH:22]=[CH:23][C:24]([S:27]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)(=[O:28])=[O:29])=[CH:25][CH:26]=1)[CH3:17]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 59610039Bromo-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 59610054(2,4-Difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl esterYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

2,4-Difluorophenol (0.38 ml, 3.89 mmol) and cesium carbonate (0.76 gm, 2.33 mmol) were taken in acetonitrile (30 ml) under argon atmosphere and was stirred for 30 minutes. Bromo-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester (1.4 gm, 3.86 mmol) in acetonitrile (15 ml) was added to the mixture and stirred at 25° C. for 3 hour. Reaction mixture was diluted with water (30 ml), extracted with ethyl acetate (3×20 ml), organic layer was washed with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a gummy mass which was purified by flash column chromatography using over silica gel using 40-60% ethyl acetate in hexane as eluent to give (2,4-difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester (1.31 gm).

Workup

  1. stirringstirred at 25° C. for 3 hour
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (3×20 ml), organic layer
  4. washwas washed with brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a gummy mass which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-bef0e2d584c74ef1a5339e35fe91ae6d
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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