Potassium Carbonate → HCID 11189483, compound

HRID 1945206Notes

Reaction equation

HRID 1945206 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:9][C:10]=1[Cl:11])[OH:8].C([O:17][C:18](=[O:21])[CH2:19]Br)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[CH3:28][S:29]([C:32]1[CH:37]=[CH:36][C:35](F)=[C:34]([Cl:39])[CH:33]=1)(=[O:31])=[O:30]>CN(C=O)C>[Cl:3][C:4]1[C:10]([Cl:11])=[CH:9][C:7]([O:8][CH2:19][C:18]([OH:17])=[O:21])=[C:6]([O:12][C:35]2[CH:36]=[CH:37][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:33][C:34]=2[Cl:39])[CH:5]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 189094,5-DichlorocatecholHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzene

Product 1

HCID 11189483HCID 11189483, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium hydride (60% wt. disp. in oil, 0.223 g) and 4,5-dichlorocatechol (1 g) in DMF (10 ml) was stirred at RT for 15 min. tert-Butyl-bromoacetate (0.9 ml) was added, stirred at RT for 2 h then potassium carbonate (0.77 g) and the product from example 7 step (ii) (0.7 g) added and the mixture heated at 90° C. for 14 h. The mixture was partitioned between 2M sodium hydroxide solution and diethylether, the aqueous layer was acidified with 2M hydrochloric acid and extracted with ethylacetate. The ethylacetate layer was dried, evaporated under reduced pressure and the residue purified by RPHPLC. Yield 0.349 g.

Workup

  1. additionwas added
  2. temperaturethe mixture heated at 90° C. for 14 h
  3. customThe mixture was partitioned between 2M sodium hydroxide solution and diethylether
  4. extractionextracted with ethylacetate
  5. dry with materialThe ethylacetate layer was dried
  6. customevaporated under reduced pressure
  7. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-72b3431059f64e66b94d40cdff98d46d
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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