Sodium Carbonate → 4-(4-Fluorophenyl)pyridine

HRID 2212996Notes

Reaction equation

HRID 2212996 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Cl.Br[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd]Cl.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 155443714-(4-Fluorophenyl)pyridineYield 117.5%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluorobenzeneboronic acid (38.7 g, 276 mmol), 4-bromopyridine hydrochloride (48.9 g, 250 mmol), [1,4-butanediylbis(diphenylphosphine-κP)] dichloropalladium (Organometallics 1998, 17, 661; 1.52 g, 2.5 mmol), 1,2-dimethoxyethane (500 mL) and sodium carbonate solution (2M, 440 mL) was degassed with bubbling nitrogen and stirred at 80° C. for 24 hours. The mixture was cooled and extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give crude title compound as a brown solid (50.87 g) which was used without further purification. 1H NMR (360 MHz, CDCl3) δ 8.65 (2H, m), 7.61 (2H, m), 7.49 (2H, dd, J 1.6, 4.6 Hz), and 7.09 (2H, m).

Workup

  1. customwas degassed with bubbling nitrogen
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7fb238ae53164a8da19215ed4f6f309e
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

Loading…