Potassium Carbonate → tert-Butyl {[4-(4-chloro-2-iodophenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamate

HRID 46320

Reaction equation

HRID 46320 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:10]=[C:11]([S:16]([N:19]([C:27]2[N:28]=[CH:29][S:30][CH:31]=2)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1F)#[N:8].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([I:40])[CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:14]2[CH:13]=[CH:12][C:11]([S:16]([N:19]([C:27]3[N:28]=[CH:29][S:30][CH:31]=3)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:17])=[CH:10][C:9]=2[C:7]#[N:8])=[C:35]([I:40])[CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6202344-Chloro-2-iodophenolHCID 59436569tert-Butyl [(3-cyano-4-fluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate

Product 1

HCID 59436631tert-Butyl {[4-(4-chloro-2-iodophenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of potassium carbonate (0.0549 g, 0.000397 mol) in N,N-dimethylformamide (3.0 mL) was added tert-butyl [(3-cyano-4-fluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 250, 0.1004 g, 0.000167 mol) and stirred at room temperature under nitrogen for 10 minutes. 4-chloro-2-iodophenol (0.067 g, 0.000263 mol) was added and stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (10.0 mL). The organic phase was washed saturated aqueous sodium chloride solution (2×10.0 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil, 162 mg, 100% yield.

Workup

  1. stirringstirred at room temperature for 16 hours
  2. washThe organic phase was washed saturated aqueous sodium chloride solution (2×10.0 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d80851a474a4ed9bbf24156d08c41b4
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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