Sodium Carbonate → 4-(2-(Trifluoromethoxy)phenyl)pyridine

HRID 505123Notes

Reaction equation

HRID 505123 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:12])([F:11])[F:10].B(O)(O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl.CO>COCCOC.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>[F:10][C:9]([F:12])([F:11])[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 27772661-Bromo-2-(trifluoromethoxy)benzeneHCID 21226129Dichloromethane methanol

Product 1

HCID 463171664-(2-(Trifluoromethoxy)phenyl)pyridineYield 51%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (commercially available) (1-bromo-2-trifluoromethoxy-benzene) in DME (first degased with argon) under argon was added 3 mol % Pd(PPh3)4, pyridyl-4-boronic acid and 2N Na2CO3, the resulting reaction mixture was vigorously stirred under reflux. After 5 h at reflux, reaction as monitored by TLC showed completion. Two phases were separated, evaporation of most of the DME, redissolution of the residue in EtOAc and washing with aq. NaOH followed by evaporation gave a yellow oil. Flash Chromatography on SiO2 gel with a mixture of CH2Cl2/MeOH gave the title compound in 51% yield.

Workup

  1. customthe resulting reaction mixture
  2. temperatureunder reflux
  3. temperatureAfter 5 h at reflux
  4. customreaction
  5. customTwo phases were separated
  6. customevaporation of most of the DME, redissolution of the residue in EtOAc
  7. washwashing with aq. NaOH
  8. customfollowed by evaporation
  9. customgave a yellow oil

Sources & evidence

ORD record
ord-4781d7a064604a9088250c56dbbcb926
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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