Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate → Ethyl 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

HRID 554214노트

반응식

HRID 554214 반응식
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

참가 물질

4

반응물 1

HCID 66924835Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 66924698Ethyl 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate수율 18.3%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

To a solution (80 mL) of ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (8.6 g) in ethanol was added 10% palladium carbon (50% containing water, 0.86 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 36 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (70 mL), 10% palladium carbon (50% containing water, 0.90 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1→5:1) to give the title compound as a brown solid (yield 1.37 g, 18%).

후처리

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol (70 mL)
  4. addition10% palladium carbon (50% containing water, 0.90 g) was added
  5. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr
  6. filtrationThe reaction mixture was filtrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1→5:1)

출처 및 근거

ORD 기록
ord-1db86f55d7134dd3a2071c9533ea1506
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048909B2

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