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

HRID 1431403ノート

反応式

HRID 1431403 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fe5471a72f8a457eaba5db4a0955be1e
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

読み込み中…