Sodium Carbonate → 2-(4-Methoxyphenyl)-4-methylpyridine

HRID 1059970Notes

Reaction equation

HRID 1059970 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 161260622-(4-Methoxyphenyl)-4-methylpyridineYield 85.8%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-bromo-4-methylpyridine (1.60 g), 4-methoxyphenylboronic acid (1.84g) and tetrakis(triphenylphosphine)-palladium (537 mg) in 1,2-dimethoxyethane (40 ml) was added 2M aqueous solution of sodium carbonate (12.1 ml). The mixture was stirred at 80° C. for 24 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 75 g, 20% ethyl acetate in n-hexane) to give 4-(4-methylpyridin-2-yl)anisole (1.59 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 75 g, 20% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-20d5e167472a4f6fb3cd7c6cc08f61d7
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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