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

HRID 1431401ノート

反応式

HRID 1431401 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[C:18]([Sn](CCCC)(CCCC)CCCC)=[N:19][CH:20]=[CH:21][CH:22]=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:18]2[C:17]([CH3:16])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:11]=1[CH3:12]

参加物

4

反応物 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

生成物 1

HCID 596311854-Chloro-5,7-difluoro-3-methyl-2-(3-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 (0.17 g, 0.685 mmol) in toluene (1.40 mL) was added 3-methyl-2-(tributylstannyl)pyridine (0.29 g, 0.75 mmol), and palladium tetrakistriphenylphosphine (0.079 g, 0.069 mmol). The reaction was stirred at 100° C. and stirring continued for 68 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-(3-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-118495e4aa124836832a2cca45f64183
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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