Methanol → Methyl 4-bromo-1H-indole-3-carboxylate

HRID 12614Notes

Reaction equation

HRID 12614 reaction equation
[CH3:1][OH:2].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH:13]=[O:14])=[CH:7][NH:8]2.[C-]#N.[Na+]>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:13]([O:2][CH3:1])=[O:14])=[CH:7][NH:8]2

Participants

6

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 27631784-Bromo-1H-indole-3-carbaldehyde

Product 1

HCID 13499091Methyl 4-bromo-1H-indole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (40 mL) solution of 4-bromo-1H-indole-3-carboaldehyde [Chem. Pharm. Bull. 33,3696 (1985)] (395 mg), sodium cyanide (432 mg) and manganese dioxide (15.3 g) were sequentially added and the mixture was stirred overnight at room temperature. To the reaction mixture, ethyl acetate (50 mL) was added and insoluble matters were removed. The filtrate was concentrated and water was added to the residue, and then the solution was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried and then concentrated. The residue was washed with diisopropyl ether and n-hexane and then concentrated to obtain the titled compound having the following physical properties (375 mg).

Workup

  1. custominsoluble matters were removed
  2. concentrationThe filtrate was concentrated
  3. additionwater was added to the residue
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed in turn with water and saturated saline
  6. customdried
  7. concentrationconcentrated
  8. washThe residue was washed with diisopropyl ether and n-hexane
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b898882e96cb45c1803327a8130cdd74
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

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