Water → HCID 23022097, compound

HRID 1787866Notes

Reaction equation

HRID 1787866 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11]C)=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].B(Br)(Br)Br.O>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 12438714Ethyl 6-methoxy-3-methyl-1H-indole-2-carboxylate

Product 1

HCID 23022097HCID 23022097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-methyl-6-methoxy-1H-indole-2-carboxylate (1.00 g; synthesized according to the disclosures in the literature (Gan et al., J. Org. Chem., vol. 62, pp. 9298-9304, 1997)) was dissolved in methylene chloride (dehydrated, 13 mL), and boron tribromide (1 M/methylene chloride, 17.2 mL) was added dropwise under ice-cooling. The resulting mixture was allowed to warm to room temperature and stirred for 40 minutes. The reaction solution was then cooled with ice, followed by addition of water. The resulting mixture was extracted with chloroform, washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (3:1-2:1 hexane/ethyl acetate) to yield the title compound (480 mg).

Workup

  1. customsynthesized
  2. temperaturecooling
  3. temperatureThe reaction solution was then cooled with ice
  4. extractionThe resulting mixture was extracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (3:1-2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1cb77ff985ea48bbb3a08fd858b47c30
Source dataset
uspto-grants-2009_03
Patent number
US07511069B2

Reaction notes

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