Sodium Methoxide → 3-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-2-methoxyquinoline

HRID 926455

반응식

HRID 926455 반응식
[N:1]1([C:6]2[CH:25]=[CH:24][C:9]([CH2:10][C:11]3[C:12](Cl)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:26][O-:27].[Na+]>C1(C)C=CC=CC=1>[N:1]1([C:6]2[CH:25]=[CH:24][C:9]([CH2:10][C:11]3[C:12]([O:27][CH3:26])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 867155943-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline2회

생성물 1

HCID 867155963-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-2-methoxyquinoline

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A heterogeneous mixture of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (13.0 g, 30.0 mmol, Intermediate 3: step c), sodium methoxide (9.73 g, 180 mmol), and toluene (120 mL) was heated at 110° C. After 5.5 hours, the mixture was cooled to room temperature then filtered through Celite® rinsing with dichloromethane. The filtrate was concentrated to provide a crude yellow solid. The crude solid was purified by flash column chromatography (silica gel, 50% dichloromethane-hexanes initially, grading to 100% dichloromethane) to provide the title compound as a white solid.

후처리

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationthen filtered through Celite®
  3. washrinsing with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customto provide a crude yellow solid
  6. customThe crude solid was purified by flash column chromatography (silica gel, 50% dichloromethane-hexanes initially

출처 및 근거

ORD 기록
ord-2003c089bd1b407b9e9270a091e04a9d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284308B2

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