Potassium Carbonate → N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188261Notes

Reaction equation

HRID 1188261 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[O:5][CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[O:1])[C:3]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=3)=[CH:4][O:5]2)=[CH:10][CH:9]=1)#[CH:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86695055N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide

Product 1

HCID 86695056N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide (1.8 g, 4.37 mmol) was dissolved in a 1:1 mixture of methanol/tetrahydrofuran (6 ml), potassium carbonate (121 mg, 0.2 eq) was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed the solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate in the presence of water. The organic phase was dried over magnesium sulfate, filtered, and solvent removed under reduced pressure to afford N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.

Workup

  1. additionwas added
  2. customwas removed under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate in the presence of water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-72b3e43661f84401a670619911af8812
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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