Sodium Carbonate → 4-Chloro-7-fluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline

HRID 1618525ノート

反応式

HRID 1618525 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:14])=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][C:22]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[CH:24][N:23]=1>O1CCOCC1.CCOC(C)=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:27]2[C:22]([CH3:21])=[N:23][CH:24]=[CH:25][CH:26]=2)[C:11]=1[CH3:12]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 164142712-Methylpyridine-3-boronic acid, pinacol esterHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

生成物 1

HCID 672852274-Chloro-7-fluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 2,4-dichloro-7-fluoro-3-methylquinoline (400 mg, 1.74 mmol) in 1,4-dioxane:water (5 mL:1 mL) was added PdCl2(PPh3)2 (122 mg, 0.17 mmol), sodium carbonate (553 mg, 5.22 mmol) and 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. The reaction was heated at reflux overnight. After this time the reaction was diluted with EtOAc (100 mL) and water (50 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexane:EtOAc, 1:0 to 1:1) gave 4-chloro-7-fluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline.

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-9ba8a23ce27e4df09260b6431e919fc8
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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