Tetrahydrofuran → 4-(4-Acetamidophenyl)pyridine

HRID 1170026Notes

Reaction equation

HRID 1170026 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C1COCC1.Cl.Br[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=2)O1>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:17]1[CH:18]=[CH:19][C:14]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27346194'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide

Product 1

HCID 205065194-(4-Acetamidophenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A round bottom flask was charged with a 2 N Na2CO3 solution (4 equivalents) and THF and the mixture was sparged with N2 through a dispersion tube. 4-Bromopyridine hydrochloride (1 equivalent) and N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide (1.2 equivalents) were subsequently added, followed by Pd(dppf)2Cl2 (2.5 mol %). The reaction mixture was refluxed overnight, cooled to room temperature and diluted with EtOAc. The two phases were separated and the organic phase was washed with a 2 N Na2CO3 solution, brine, and dried (Na2SO4). Evaporation of the solvent under reduced pressure and purification by silica gel chromatography afforded the desired product as a white solid. MH+=213.1.

Workup

  1. customthe mixture was sparged with N2 through a dispersion tube
  2. temperatureThe reaction mixture was refluxed overnight
  3. customThe two phases were separated
  4. washthe organic phase was washed with a 2 N Na2CO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-545f5e64cb4f4346a7341e2ddcb4df07
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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