2-Methyl-6-(tributylstannyl)pyridine → 4-Chloro-5,7-difluoro-3-methyl-2-(6-methylpyridin-2-yl)quinoline

HRID 1431403노트

반응식

HRID 1431403 반응식
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[N:18]=1>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([CH3:16])[N:18]=2)[C:11]=1[CH3:12]

참가 물질

4

반응물 2

HCID 114631832-Methyl-6-(tributylstannyl)pyridineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

생성물 1

HCID 596312274-Chloro-5,7-difluoro-3-methyl-2-(6-methylpyridin-2-yl)quinoline

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.2 g, 0.806 mmol) in toluene (1.60 mL) was added 2-methyl-6-(tributylstannyl)pyridine (0.34 g, 0.89 mmol), and palladium tetrakistriphenylphosphine (0.093 g, 0.081 mmol). The reaction was stirred at 100° C. and stirring continued for 18 h. The reaction mixture was cooled to rt and concentrated in vacuo. The crude material was purified by column chromatography on silica gel, eluting with (0-50% EtOAc in hexanes) to provide 4-chloro-5,7-difluoro-3-methyl-2-(6-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

후처리

  1. stirringstirring
  2. temperatureThe reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by column chromatography on silica gel
  5. washeluting with (0-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-fe5471a72f8a457eaba5db4a0955be1e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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