Potassium Carbonate → 4-Chloro-5,7-difluoro-3-methyl-2-(4-pyridinyl)quinoline

HRID 1431405ノート

反応式

HRID 1431405 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.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>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][N:16]=[CH:17][CH:18]=2)[C:11]=1[CH3:12]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

生成物 1

HCID 596313124-Chloro-5,7-difluoro-3-methyl-2-(4-pyridinyl)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 (1.0 g, 4.03 mmol) in toluene (8.06 mL) was added pyridin-4-ylboronic acid (0.743 g, 6.05 mmol), potassium carbonate (1.11 g, 8.06 mmol) and palladium tetrakistriphenylphosphine (0.466 g, 0.403 mmol). The reaction was stirred at 100° C. and stirring continued for 15 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-(4-pyridinyl)quinoline as a white solid. Mass Spectrum (ESI) m/e=291.1 (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-775584e9ef8a45118125af1b3dd6f91d
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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