Dimethylformamide → 4-[(E)-2-(4-fluorophenyl)vinyl]-2-(4-methoxybenzyloxy)-pyridine

HRID 15050

反応式

HRID 15050 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.I[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH:23]=1>[Cl-].[Na+].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>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:7]/[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[CH:23]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678834-FluorostyreneHCID 668729534-Iodo-2-((4-methoxybenzyl)oxy)pyridine

生成物 1

HCID 668727254-[(E)-2-(4-fluorophenyl)vinyl]-2-(4-methoxybenzyloxy)-pyridine収率 61%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

4-Fluorostyrene (3.0 mL), dichlorobis(triphenylphosphine)palladium (870 mg) and potassium carbonate (5.2 g) were added to DMF (70 mL) solution of 4-iodo-2-(4-methoxybenzyloxy)pyridine (4.25 g) 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 resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4) to provide the title compound (2.55 g, 61%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. concentrationConcentrating the solvent under reduced pressure
  4. customthe resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4)

出典と根拠

ORDレコード
ord-59420ad30a3644888fc89d1d064672b1
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

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