Cesium carbonate → HCID 58355509, compound

HRID 2168870Notes

Reaction equation

HRID 2168870 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]C)=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O>CC(N(C)C)=O>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 70992Methyl 1H-indole-2-carboxylateHCID 116870064-Methoxybutyl methanesulfonate

Product 1

HCID 58355509HCID 58355509, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 1H-indole-2-carboxylate (0.67 g), cesium carbonate (1.9 g) and 4-methoxybutyl methanesulfonate (0.70 g) were suspended in DMA (20 ml), and the suspension was stirred at 60° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (0:10-4:6) was concentrated under reduced pressure. The obtained residue was dissolved in methanol (10 ml), 4N aqueous sodium hydroxide solution (5 ml) was added, and the mixture was heated at 80° C. for 2 hr. The mixture was allowed to cool to room temperature, acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the object product (0.77 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (0:10-4:6)
  8. concentrationwas concentrated under reduced pressure
  9. dissolutionThe obtained residue was dissolved in methanol (10 ml)
  10. addition4N aqueous sodium hydroxide solution (5 ml) was added
  11. temperaturethe mixture was heated at 80° C. for 2 hr
  12. temperatureto cool to room temperature
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with saturated brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c090cc5fdc734e7aa3d2295cc3d76f2c
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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