Sodium Carbonate → HCID 68565294, compound

HRID 1786468Notes

Reaction equation

HRID 1786468 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10](Br)[CH:9]=2)=[O:5].[CH3:25]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([CH3:25])[CH:9]=2)=[O:5]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 574072TrimethylboroxineHCID 68565015HCID 68565015, compound

Product 1

HCID 68565294HCID 68565294, compoundYield 57%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.20 g (0.50 mmol) 6-bromo-5-methoxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 8 mL 1,2-dimethoxyethane were added 58 μg (0.050 mmol) tetrakis(triphenylphosphine)palladium(0). After stirring 30 min at room temperature, 76 μg (0.60 mmol) trimethylboroxine and 0.16 g (1.50 mmol) sodium carbonate dissolved in 4 mL water were added and the reaction mixture was heated 3 h at reflux. The solution was poured into 10% aqueous sodium bicarbonate solution and ethyl acetate, the layers were separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified twice by flash chromatography on silica gel using a gradient of dichloromethane:methanol (100:0 to 50:50 v/v) as eluant, to afford 95 mg (57%) of the title compound as colourless oil.

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was heated 3 h
  3. temperatureat reflux
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified twice by flash chromatography on silica gel using a gradient of dichloromethane:methanol (100:0 to 50:50 v/v) as eluant

Sources & evidence

ORD record
ord-e60f90ba2ed04fd082d42f89de8183e3
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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