Cerous carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-7-methoxyquinazoline

HRID 56485

반응식

HRID 56485 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([Cl:14])[N:6]=[CH:5]2.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.C(=O)([O-])[O-].[Ce+3].C(=O)([O-])[O-].C(=O)([O-])[O-].[Ce+3]>C1COCC1.O1CCOCC1.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:14][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([C:19]3[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=3)[CH:3]=2)[N:8]=1

참가 물질

8

반응물 3

HCID 160516Cerous carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 591992766-Bromo-2-chloro-7-methoxyquinazoline

생성물 1

HCID 867135952-Chloro-6-(3,5-dimethoxyphenyl)-7-methoxyquinazoline수율 38%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 6-bromo-2-chloro-7-methoxyquinazoline (2.4 g, 8.82 mmol), 3,5-dimethoxyphenylboronic acid (1.6 g, 8.82 mmol), cerium carbonate (8.6 g, 26.46 mmol) and Pd(PPh3)2Cl2 (1.4 g, 2.1 mmol) in THF (10 mL), dioxane (10 mL) and water (2 mL) was degassed with nitrogen three times and stirred at 85° C. for 3 hours. The mixture was cooled to room temperature and extracted with dichloromethane (3×50 mL). The organic layers were separated, combined, washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether: ethyl acetate=1:4) to give the title compound (1.1 g, 38%) as a white solid. MS (ES+) C17H15ClN2O3 requires: 330, 332, found: 331, 333 [M+H]+.

후처리

  1. customwas degassed with nitrogen three times
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with dichloromethane (3×50 mL)
  4. customThe organic layers were separated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (petroleum ether: ethyl acetate=1:4)

출처 및 근거

ORD 기록
ord-fb0b40146cf3467a9e78535ac537d0ab
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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