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

HRID 420140Notes

Reaction equation

HRID 420140 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([OH:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[C:19]([O-])([O-])=O.[K+].[K+].CN(C=O)C.CI>CCOC(C)=O>[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:18][CH3:19])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

Product 1

HCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 14.56 g of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate and 16.2 g of K2CO3 and 220 ml of DMF was added 7.48 ml of MeI and the mixture was stirred at 60° C. for 3 hrs. The mixture was allowed to cool, diluted with EtOAc, washed with water and saturated brine successively, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (n-hexane-EtOAc) to afford 15.15 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate as a pale yellow oil.

Workup

  1. temperatureto cool
  2. washwashed with water and saturated brine successively
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified on SiO2 column chromatography (n-hexane-EtOAc)

Sources & evidence

ORD record
ord-0eb400ffa6964be08a89773913045090
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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