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

HRID 1431405노트

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HRID 1431405 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 596313124-Chloro-5,7-difluoro-3-methyl-2-(4-pyridinyl)quinoline

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-775584e9ef8a45118125af1b3dd6f91d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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