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

HRID 15050
Notes
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Reaction equation

HRID 15050 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-59420ad30a3644888fc89d1d064672b1
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732456B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes