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

HRID 15056

反応式

HRID 15056 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-176101cd28c147d0814db60ad04c21e6
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

関連ノート

読み込み中…