Cesium carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline

HRID 524081노트

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HRID 524081 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([Cl:13])[N:6]=[CH:5]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.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:7]1[N:6]=[CH:5][C:4]2[C:9](=[C:10]([F:12])[CH:11]=[C:2]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[CH:3]=2)[N:8]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 591992866-Bromo-2-chloro-8-fluoroquinazoline

생성물 1

HCID 867135972-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline수율 51%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of 6-bromo-2-chloro-8-fluoroquinazoline (4.0 g, 15.4 mmol), 3,5-dimethoxyphenylboronic acid (4.47 g, 16.9 mmol), cesium carbonate (10.0 g, 30.8 mmol) and Pd(PPh3)2Cl2 (236 mg, 0.77 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 3 h. Both TLC and LCMS showed the reaction was completed. The reaction mixture was cooled to RT and directly concentrated. The residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1) to afford the title compound (2.5 g, 51%) as a yellow solid. MS (ES+) C16H12ClFN2O2 requires: 318/320. found: 319/321 [M+H]+.

후처리

  1. customwas degassed with nitrogen three times
  2. temperatureThe reaction mixture was cooled to RT
  3. concentrationdirectly concentrated
  4. customThe residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1)

출처 및 근거

ORD 기록
ord-fd87a471369f43e8926b3f171e908065
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340514B2

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