Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → HCID 136409080, compound

HRID 872121Notes

Reaction equation

HRID 872121 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([NH2:15])[NH:5][N:4]=1)[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][C:25](OCC)=[O:26])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]2[NH:15][C:25](=[O:26])[CH:24]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)[N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 178438047HCID 178438047, compound

Product 1

HCID 136409080HCID 136409080, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Ethyl-4-(4-methylphenyl)-1H-pyrazol-5-amine (200 mg) and ethyl 3-(4-fluorophenyl)-3-oxopropanoate (250 mg) are stirred overnight in a pyridine (10 mL) solvent at 95° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield 280 mg of the target compound.

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-d111eb25bb8f41ccb9a0fc6b6981ce1b
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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