Potassium Carbonate → 3-Bromo-5-ethylpyridine

HRID 555995Notes

Reaction equation

HRID 555995 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](B(O)O)[CH3:16]>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].[Ag-]=O.C1COCC1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([CH2:15][CH3:16])[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 693693,5-DibromopyridineHCID 521157Ethylboronic acid

Product 1

HCID 6428043-Bromo-5-ethylpyridine

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418778HCID 178418778, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3,5-dibromo-pyridine (0.4 g, 1.688 mmol), potassium carbonate (0.7 g, 5.064 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.138 g, 0.169 mmol), silver(I) oxide (0.902 g, 4.22 mmol), ethyl boronic acid (0.150 g, 2.03 mmol) and THF (8 ml) are mixed together, purged with argon and heated to reflux overnight. After cooling to room temperature the reaction mixture is filtered through Celite® (filter agent) washing with DCM. The DCM is reduced in vacuo and the residue is purified by flash chromatography by loading onto a 20 g silica column eluting with DCM to afford the title compound, [MH+ 185.91 and 187.91].

Workup

  1. custompurged with argon
  2. temperatureheated
  3. temperatureto reflux overnight
  4. filtrationis filtered through Celite® (filter agent)
  5. washwashing with DCM
  6. customthe residue is purified by flash chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-02fb406c602a4af6b6e2a0b34182214a
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

Loading…