Potassium Carbonate → 4-(6-Chloro-pyridin-2-yloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 1929192Notes

Reaction equation

HRID 1929192 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](Cl)[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[N:25]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 169892,6-DichloropyridineHCID 596001381-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylate

Product 1

HCID 860660324-(6-Chloro-pyridin-2-yloxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

159 (500 mg, 1.6 mmol), 2,6-Dichloro-pyridine (360 mg, 24 mmol) are dissolved in 15 ml of dimethylformamide. After addition of potassium carbonate (340 mg, 24 mmol) and a catalytic amount Cu-powder the mixture is heated to 160° C. for 3 hours. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and washed with water. The organic layers are dried over sodium sulphate and evaporated. The crude product is solved in dichloromethane and after evaporation crystallized with cyclohexane.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layers are dried over sodium sulphate
  4. customevaporated
  5. customafter evaporation
  6. customcrystallized with cyclohexane

Sources & evidence

ORD record
ord-0fa053d2174443f1a49f0ae1930c40af
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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