Triethylamine → HCID 67395699, compound

HRID 1426685Notes

Reaction equation

HRID 1426685 reaction equation
Cl[C:2]1[NH:3][C:4]([C:13]2[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C>C(O)C.[C].[Pd]>[F:19][C:14]1[C:13]([C:4]2[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]=2[CH3:12])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67399142HCID 67399142, compound

Product 1

HCID 67395699HCID 67395699, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-chloro-5-(2-fluoropyridin-3-yl)-4-methyl-1H-pyrrole-3-carboxylate (10.0 g) and triethylamine (5.5 mL) in ethanol (250 mL) was added 10% palladium carbon (50% containing water, 1.43 g), and the mixture was stirred under a hydrogen atmosphere at 60° C. for 3 hr. After cooling, the reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as colorless crystals (yield 7.93 g, 90%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c5fd8623d36f4c08a88c618dee7c1e5a
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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