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

HRID 1590094Notes

Reaction equation

HRID 1590094 reaction equation
[C:1]1([C:7]2[CH:12]=[N+:11]([O-])[C:10]([CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-].[Cl:23]C1C=CC(B(O)O)=CC=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:23][C:4]1[CH:5]=[CH:6][C:1]([C:7]2[CH:8]=[CH:9][C:10]([CH3:14])=[N:11][CH:12]=2)=[CH:2][CH:3]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 149805285-Phenyl-2-picoline N-oxide

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-9a1ce540832d42acad73b1a8bff37a48
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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