Toluene → 2-(4-Chloro-phenyl)-3-fluoro-pyridine

HRID 1626422Notes

Reaction equation

HRID 1626422 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 666786032-(4-Chloro-phenyl)-3-fluoro-pyridineYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

2-Chloro-3-fluoropyridine (0.4380 g, 3.33 mmol), 4-chlorophenylboronic acid (0.6248 g, 3.996 mmol), palladium tetrakistriphenylphosphine (0.1924 g, 0.1665 mmol), sodium carbonate (0.4235 g, 3.996 mmol), toluene (10 mL), and water (1 mL) were placed in a teflon lined vial. The vial was sealed and stirred at 125° C. for 21 hour. The mixture was cooled to ambient temperature and the whole mixture was purified on silica gel (EtOAc-hexanes gradient) to provide 569.4 mg of the title compound as white solid (82%).

Workup

  1. customThe vial was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. customthe whole mixture was purified on silica gel (EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-1e7ca6df9ae14306af6c863930fe658b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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