Dimethylformamide → Methyl 4-bromo-3-formyl-1H-indole-2-carboxylate

HRID 1013301Notes

Reaction equation

HRID 1013301 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.O=P(Cl)(Cl)Cl.CN(C)[CH:22]=[O:23]>ClCCl.C(OCC)(=O)C.C([O-])(=O)C.[Na+].O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:22]=[O:23])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 4714973methyl 4-bromo-1H-indole-2-carboxylate

Product 1

HCID 71463951Methyl 4-bromo-3-formyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 517045Sodium AcetateSolvent

Procedure

To a solution of methyl 4-bromo-1H-indole-2-carboxylate (4.09 g) in dichloromethane (60 mL) was added a mixture of POCl3 (3.7 g) and N,N-dimethylformamide (1.76 g). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (300 mL) and 2M sodium acetate solution in water (200 mL). The mixture was stirred thoroughly for 1 hour. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the mixture gave the title compound, which was used in next step without purification.

Workup

  1. temperatureat reflux overnight
  2. stirringThe mixture was stirred thoroughly for 1 hour
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined extracts were washed with water (×3), brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration, concentration of the mixture

Sources & evidence

ORD record
ord-a086746c2c13489093703c3e9d9cd3c2
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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