ethyl 2-bromo-3-oxo-3-phenylpropanoate → HCID 66856132, compound

HRID 1530009Notes

Reaction equation

HRID 1530009 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[C:3]([C:10](=[S:12])[NH2:11])[CH:2]=1.Br[CH:14]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[C:3]([C:10]2[S:12][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateHCID 46840049Pyrazolo[1,5-a]pyridine-3-carbothioamide

Product 1

HCID 66856132HCID 66856132, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of commercially available pyrazolo[1,5-a]pyridine-3-carbothioamide (580 mg, 3.3 mmol) in ethanol (20 mL) was added ethyl 2-bromo-3-oxo-3-phenylpropanoate (1.0 g, 3.7 mmol), and the mixture was heated under reflux for 11 hr. The reaction solution was allowed to cool to room temperature, and the resulting solid was collected by filtration and washed with methanol. The collected filtrate and washing solution was concentrated under reduced pressure, and the obtained residue was suspended in ethyl acetate (100 mL). The obtained suspension was washed with saturated aqueous sodium bicarbonate solution (50 mL×2), and the collected aqueous layer was extracted with ethyl acetate (50 mL). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→100/0) to give the title compound (360 mg, 31%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hr
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with methanol
  5. washThe collected filtrate and washing solution
  6. concentrationwas concentrated under reduced pressure
  7. washThe obtained suspension was washed with saturated aqueous sodium bicarbonate solution (50 mL×2)
  8. extractionthe collected aqueous layer was extracted with ethyl acetate (50 mL)
  9. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  10. filtrationthe insoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→100/0)

Sources & evidence

ORD record
ord-7b7efa0cdc994e31bddaea7c7b44a44b
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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