Water → HCID 23022097, compound

HRID 1817382Notes

Reaction equation

HRID 1817382 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-894c6ca92c6b416284930e42f3757102
Source dataset
uspto-grants-2009_10
Patent number
US07598284B2

Reaction notes

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