Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → HCID 136393912, compound

HRID 872132Notes

Reaction equation

HRID 872132 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][NH:11][C:12]=2[NH2:13])=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][C:23](OCC)=[O:24])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:10][N:11]3[C:21]([C:18]4[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=4)=[CH:22][C:23](=[O:24])[NH:13][C:12]=23)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 47372344-(4-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 136393912HCID 136393912, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(4-Methylphenyl)-1H-pyrazol-5-amine (170 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 180 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-fa06c9efde4e49a4bb36ec7fbf116e7d
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

Loading…