Dimethylformamide → ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

HRID 420144Notes

Reaction equation

HRID 420144 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[CH:11]=[CH:10]2)[CH2:8][CH2:7]1.CN([CH:28]=[O:29])C>CCOC(C)=O.[OH-].[Na+]>[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[C:11]([CH:28]=[O:29])=[CH:10]2)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate

Product 1

HCID 86621575ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

1.28 ml of POCl3 was added dropwise to a solution of 3.24 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate in 30 ml of DMF and the mixture was stirred at 0° C. for 2 hrs. The mixture was diluted with EtOAc and 25 ml of 1N NaOH was added. Then the mixture was made basic using saturated NaHCO3aq. The mixture was extracted with EtOAc and the extract was washed with water and saturated brine, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system) to give 2.4 g of ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system)

Sources & evidence

ORD record
ord-ce40d6d2c83442999f30661b6b7ba9a4
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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