Sodium Carbonate → 4-[2-(4-Fluorophenyl)ethyl]-2-(4-methoxybenzyloxy)-pyridine

HRID 15056

반응식

HRID 15056 반응식
[CH:1]12B[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3]C2.FC1C=CC(C=C)=CC=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][N:31](C3C=CC(OCCN4CCCC4)=CC=3)[C:30](=[O:48])[CH:29]=2)=[CH:22][CH:21]=1.[C:49](=O)([O-])[O-:50].[Na+].[Na+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.C1COCC1>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[C:30]([O:48][CH2:1][C:8]3[CH:3]=[CH:4][C:5]([O:50][CH3:49])=[CH:6][CH:7]=3)[CH:29]=2)=[CH:24][CH:25]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 678834-FluorostyreneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 111888914-[(e)-2-(4-Fluorophenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1h-pyridin-2-one

생성물 1

HCID 684311084-[2-(4-Fluorophenyl)ethyl]-2-(4-methoxybenzyloxy)-pyridine수율 100%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

9-Borabicyclo[3.3.1]nonane (540 mg) was added to THF solution (5 mL) of 4-fluorostyrene (240 mL) and stirred at room temperature for 2 hours. To the reaction liquid, the compound synthesized in Step (1) of Example 45(340 mg), tetrakis(triphenylphosphine)palladium (60 mg), DMF (5 mL) and 2M aqueous sodium carbonate solution (1 mL) were added and stirred at 100° C. for 19 hours. Saturated brine was added to the reaction liquid, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4) to provide the title compound (336 mg, 100%).

후처리

  1. customTo the reaction liquid
  2. stirringstirred at 100° C. for 19 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. concentrationConcentrating the solvent under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

출처 및 근거

ORD 기록
ord-176101cd28c147d0814db60ad04c21e6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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