Potassium Carbonate → HCID 86605576, compound

HRID 2243509Notes

Reaction equation

HRID 2243509 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[S:11][C:10]([C:12]#[N:13])=[C:9]([OH:14])[C:7]=3[S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[S:11][C:10]([C:12]#[N:13])=[C:9]([O:14][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:7]=3[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68547903HCID 68547903, compound

Product 1

HCID 86605576HCID 86605576, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-chloro-3-hydroxythieno[3,2-b][1]benzothiophene-2-carbonitrile (200 mg, 0.8 mmol), potassium carbonate (156 mg, 1.5 eq), methyl bromoacetate (110 μL, 1.5 eq) in DMF was heated at 60° C. for 1.5 h. The solution was diluted with ethyl acetate, washed with water and brine, dried, filtered, evaporated, and flash chromatographed (20-30% ethyl acetate/hexanes) to provide methyl [(6-chloro-2-cyanothieno[3,2-b][1]benzothien-3-yl)oxy]acetate (230 mg, 90%) as a white, fibrous solid.

Workup

  1. washwashed with water and brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customflash chromatographed (20-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-706109ea166b44188ac1ba0298f3abdf
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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