Sodium Bicarbonate → HCID 21717241, compound

HRID 1386351Notes

Reaction equation

HRID 1386351 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].Br[C:22]1[CH:30]=[C:29]2[C:25]([CH2:26][C:27](=[O:31])[NH:28]2)=[CH:24][CH:23]=1>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:22]1[CH:30]=[C:29]2[C:25]([CH2:26][C:27](=[O:31])[NH:28]2)=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 21717241HCID 21717241, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-t-Butoxycarbonylpyrrol-2-ylboronic acid (1.5 g, 7.1 mmol) and a saturated aqueous solution of sodium hydrogen carbonate (25 ml) were added to a solution of 6-bromooxindole (1.1 g, 5.2 mmol), (prepared as described for the starting material in Example 62), in 1,2-dimethoxyethane (75 ml). The reaction mixture was degassed and placed under argon and tetrakis(triphenylphosphine)palladium(0) (50 mg) was added and the mixture heated at reflux for 6 hours. The organic solvent was removed by evaporation and the reaction mixture partitioned between ethyl acetate and water. The organic phase was separated and the aqueous phase was re-extracted twice with ethyl acetate. The organic phases were combined, washed with brine, dried (MgSO4), and the solvent removed by evaporation. The residue was triturated with ether/isohexanes (1/1) and collected by filtration to give 6-(1-t-butoxycarbonylpyrrol-2-yl)oxindole (1.11 g, 71%).

Workup

  1. custom(prepared
  2. customThe reaction mixture was degassed
  3. additiontetrakis(triphenylphosphine)palladium(0) (50 mg) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 6 hours
  6. customThe organic solvent was removed by evaporation
  7. customthe reaction mixture partitioned between ethyl acetate and water
  8. customThe organic phase was separated
  9. extractionthe aqueous phase was re-extracted twice with ethyl acetate
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent removed by evaporation
  13. customThe residue was triturated with ether/isohexanes (1/1)
  14. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a450541c5b354cfabe68fd18af0cd083
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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