Water → HCID 68496088, compound

HRID 1038750Notes

Reaction equation

HRID 1038750 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14]C)[CH:8]=2)=[O:4].[H-].[Na+].I[CH3:19].O>CN(C)C=O.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

Product 1

HCID 68496088HCID 68496088, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methoxy-1H-indole-2-carboxylic acid methyl ester (11.57 g, 56.38 mmol) in N,N-dimethylformamide (DMF) (100 mL) was added 60% sodium hydride in oil (2.93 g, 73.29 mmol) under ice cooling. After the mixture was stirred for 15 minutes, iodomethane (3.86 mL, 62.02 mmol) was added and the mixture was stirred at the same temperature for 1 hour. To the mixture were added water and diethyl ether (Et2O), and then resulting precipitate was collected by filtration. The white precipitate was dissolved in dichloromethane (200 mL), and to the solution was added dropwise boron tribromide dichloromethane solution (100 mL) while ice cooling under an argon atmosphere. The reaction mixture was stirred at the same temperature for 1 hour, and then quenched with methanol (MeOH). The solvent was evaporated in vacuo, and water was added to the residue. The aqueous mixture was extracted with ethyl acetate (AcOEt). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 10.19 g of the title compound as a brown powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. customresulting precipitate
  3. filtrationwas collected by filtration
  4. dissolutionThe white precipitate was dissolved in dichloromethane (200 mL)
  5. additionto the solution was added dropwise boron tribromide dichloromethane solution (100 mL) while ice cooling under an argon atmosphere
  6. stirringThe reaction mixture was stirred at the same temperature for 1 hour
  7. customquenched with methanol (MeOH)
  8. customThe solvent was evaporated in vacuo, and water
  9. additionwas added to the residue
  10. extractionThe aqueous mixture was extracted with ethyl acetate (AcOEt)
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-10544095ec564365bf813ac7873d8a06
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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