Ethyl Acetate → 5-cyclopropylmethoxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 74451Notes

Reaction equation

HRID 74451 reaction equation
[CH:1]1([CH2:4]Br)[CH2:3][CH2:2]1.[CH2:6]([O:8][C:9]([C:11]1[N:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([OH:20])=[CH:15][CH:14]=2)=[O:10])[CH3:7].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[CH2:6]([O:8][C:9]([C:11]1[N:12]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([O:20][CH2:4][CH:1]1[CH2:3][CH2:2]1)=[CH:15][CH:14]=2)=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 680059685-hydroxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 680054435-cyclopropylmethoxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropylmethyl bromide (0.072 ml, 0.75 mmol) was added to a suspension (5.0 ml) of 5-hydroxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (173 mg, 0.48 mmol) and potassium carbonate (276 mg, 1.0 mmol) in acetonitrile, and stirred at 80° C. for five hours. After cooling to room temperature, the reaction mixture was combined with ethyl acetate and water and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 5-cyclopropylmethoxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester as a colorless gum-like material (112.5 mg, 56%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5698e2d3fa1346cf8ceba705af681229
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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