HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 15056
Notes
Print preview

Reaction equation

HRID 15056 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents

4
HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-176101cd28c147d0814db60ad04c21e6
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732456B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes