Potassium Carbonate → 4-(3,5-Difluoro-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 1929180Notes

Reaction equation

HRID 1929180 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]=[C:21]([N+:23]([O-:25])=[O:24])[C:20]([F:26])=[CH:19][C:18]=1[F:27].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:22]1[CH:17]=[C:18]([F:27])[CH:19]=[C:20]([F:26])[C:21]=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 750121,2,4-Trifluoro-5-nitrobenzeneHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668421024-(3,5-Difluoro-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 (1 g, 4.87 mmol) and 1,2,4-Trifluoro-5-nitro-benzene (0.559 ml, 4.87 mmol) are dissolved in 10 ml of dimethylformamide. After addition of potassium carbonate (1.3 g, 9.74 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.

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

Sources & evidence

ORD record
ord-9d9403163a414128a911e26e3d9d2cce
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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