HCID 66924771, compound → HCID 66924741, compound

HRID 554216Notes

Reaction equation

HRID 554216 reaction equation
Cl.Cl[C:3]1[NH:4][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C.[C].[Pd]>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:5]1[NH:4][CH:3]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=1

Participants

4

Reactant 1

HCID 66924771HCID 66924771, compound

Product 1

HCID 66924741HCID 66924741, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-chloro-5-(pyridin-2-yl)-1H-pyrrole-3-carboxylate hydrochloride (2.73 g) was dissolved in ethanol (200 mL), and 10% palladium carbon (50% containing water, 2.73 g) was added under a nitrogen atmosphere. Under a hydrogen atmosphere, the mixture was stirred at 50° C. for 15 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogencarbonate was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as colorless crystals (yield 1.73 g, 84%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionSaturated aqueous sodium hydrogencarbonate was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2bdd7e1e3bc24670a634edddc9c44525
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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