Toluene → 6-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

HRID 74459

Reaction equation

HRID 74459 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:4].[CH3:25][C:26](P(C(C)(C)C)C1C=CC=CC=1)([CH3:28])C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH:28]1[CH2:26][CH2:25]1)[CH:8]=2)=[O:4]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 316378Di-tert-butylphenylphosphineHCID 680048106-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 680048306-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Predetermined amounts of 6-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester (300 mg, 0.73 mmol), palladium acetate (16.5 mg, 0.07 mmol), bis(1,1-dimethylethyl)phenylphosphine (0.028 ml, 0.12 mmol), potassium cyclopropyl trifluoroborate (163 mg, 1.1 mmol), and cesium carbonate (718 mg, 2.2 mmol) were placed in a reaction container, and toluene (5 ml) and water (0.5 ml) were added thereto. The resulting mixture was then stirred at 100° C. for 14 hours. After cooling it to room temperature, the mixture was diluted with ethyl acetate, and washed twice with water, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3). Thus, a yellow solid was obtained (208 mg, 77%).

Workup

  1. additionwere added
  2. temperatureAfter cooling it to room temperature
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3)
  8. customThus, a yellow solid was obtained (208 mg, 77%)

Sources & evidence

ORD record
ord-fb17bd2a5fb640e9b9ec8cb20bfeb4f5
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Linked notes

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