Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → HCID 136393910, compound

HRID 872133Notes

Reaction equation

HRID 872133 reaction equation
[CH2:1]([C:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:8]([NH2:17])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:1]([C:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[C:8]2[NH:17][C:27](=[O:28])[CH:26]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=3)[N:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 178441975HCID 178441975, compound

Product 1

HCID 136393910HCID 136393910, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Butyl-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 215 mg of the target compound is yielded by column chromatography.

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

Sources & evidence

ORD record
ord-6c726c1157e847d5abee6b13e3ed671d
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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