Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate → Ethyl 3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)propanoate

HRID 2068959

Reaction equation

HRID 2068959 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)[N:4]2[C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=[C:3]12>[C].[Pd].C(O)(=O)C>[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:14])([F:13])[F:15])[CH:9]=2)[N:4]2[C:16]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=[C:3]12

Participants

4

Reactant 1

HCID 59198853Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate

Product 1

HCID 59198598Ethyl 3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)propanoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl (E)-3-(4-oxo-7-trifluoromethyl-4,5-dihydropyrrolo[1,2-a]-quinoxalin-1-yl)acrylate as synthesized in Example 188, 182 mg, 5% palladium carbon 80 mg and acetic acid 6 mL were mixed and stirred under hydrogen atmosphere at room temperature for 16 hours. Filtering the reaction liquid through Celite, 50 mL of water was added to the filtrate and the precipitated crystals were recovered by filtration. The crystals were washed successively with water and diethyl ether, and dried in flowing air under heating to provide 120 mg of the title compound.

Workup

  1. additionwere mixed
  2. filtrationFiltering
  3. customthe reaction liquid through Celite, 50 mL of water
  4. additionwas added to the filtrate
  5. filtrationthe precipitated crystals were recovered by filtration
  6. washThe crystals were washed successively with water and diethyl ether
  7. customdried
  8. temperatureunder heating

Sources & evidence

ORD record
ord-f2f44feaddf04ad1b3d1c9a6937063da
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Linked notes

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