Sodium Carbonate → 5-(4-Chlorophenyl)-2-methylpyridine

HRID 1034299Notes

Reaction equation

HRID 1034299 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-].[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O.CCO>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=2)=[CH:27][CH:26]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 145472812-Methyl-5-pyridinetrifluoromethanesulfonate

Product 1

HCID 123670755-(4-Chlorophenyl)-2-methylpyridine

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The trifluoromethane sulfonate from Step 1 (500 mg) was dissolved in 10 mL of toluene, 5 mL of EtOH, and 1.6 mL of 2M aqueous Na2CO3. Then 203 mg LiCl, 411 mg of 4-chlorobenzeneboronic acid (Lancaster) and 832 mg of tetrakis (triphenylphosphine) palladium were added successively. The resulting reaction mixture was heated up to 90°-95° C. for 1 hour. The reaction mixture was cooled down to room temperature, EtOAc was added, and the organic phase was washed with 1N NaOH, brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography using hexane: EtOAc 3:2 gave the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated up to 90°-95° C. for 1 hour
  3. washthe organic phase was washed with 1N NaOH, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-f3bf2e195dcc4932ac95d189b72d1e1d
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

Loading…