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

HRID 1618525노트

반응식

HRID 1618525 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ba8a23ce27e4df09260b6431e919fc8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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