Potassium Carbonate → 4-(2-Nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2267864Notes

Reaction equation

HRID 2267864 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668421164-(2-Nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-1H-indole-2-carboxylic acid ethyl ester (0.5 g, 2.436 mmol) and 2-fluoro-nitro-benzene (0.257 ml, 2.436 mmol) are dissolved in 10 ml of dimethylformamide. After addition of potassium carbonate (0.67 g, 4.87 mmol) the mixture is stirred over night at room temperature. Then the reaction mixture is evaporated under reduced pressure, dissolved with ethyl acetate and washed with water. The organic layers are dried over sodium sulfate and evaporated. The crude product is used in the next step without further purification.

Workup

  1. customThen the reaction mixture is evaporated under reduced pressure
  2. dissolutiondissolved with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. customevaporated
  6. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-dab44557c957494c8c88c122ffcff627
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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