1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 1404192노트

반응식

HRID 1404192 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8](/[CH:15]=[CH:16]/[C:17](=O)[C:18]([F:21])([F:20])[F:19])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:15]=[CH:16][C:17]([C:18]([F:21])([F:20])[F:19])=[C:9]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 90442473(E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate

생성물 1

HCID 90407010ethyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
120 °C

실험 절차

To a solution of (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate (0.95 g, 2.83 mmol) in EtOAc (20 mL) was added DBU (0.85 mL, 5.66 mmol) and the resulting mixture heated in a sealed tube for 90 min at 120° C. The resulting mixture was cooled to room temperature, diluted with EtOAc (80 mL) and washed with 5% KHSO4 (2×80 mL) and brine (80 mL). The organic layer was concentrated and the residue purified by elution from a 25-g silica cartridge with 0-20% EtOAc/heptane to yield ethyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate as a white solid.

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. washwashed with 5% KHSO4 (2×80 mL) and brine (80 mL)
  3. concentrationThe organic layer was concentrated
  4. customthe residue purified by elution from a 25-g silica cartridge with 0-20% EtOAc/heptane

출처 및 근거

ORD 기록
ord-17244d9577784929a457a3a5b3033fba
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912227B1

반응 노트

불러오는 중…