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

HRID 1929174Notes

Reaction equation

HRID 1929174 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][C:20]([F:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].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][C:20]([F:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677672,5-DifluoronitrobenzeneHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668417904-(4-Fluoro-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 (0.92 g, 4.483 mmol) and 1,4-Difluoro-2-nitro-benzene (0.486 ml, 4.483 mmol) are dissolved in 10 ml of dimethylformamide. After addition of potassium carbonate (1.2 g, 8.96 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-b03185cff4214613a63b44afd632c370
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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