Sodium Carbonate → 4-(2-Methoxy-5-nitrophenyl)pyridine

HRID 1358944Notes

Reaction equation

HRID 1358944 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 788702-Bromo-4-nitroanisoleHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 144519694-(2-Methoxy-5-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 2-bromo-4-nitroanisole (7.6 g, 32.7 mmol), 4-pyridineboronic acid (4.07 g, 33 mmol) and powdered sodium carbonate (13.8 g, 5 equivalents) in 1:1 1,2-dimethoxyethane:water (1,360 ml) was degassed for 0.5 hr, by the passage of a stream of argon. Tetrakistriphenylphosphine palladium (0) (1.35 g) was added, and the mixture was cooled, the solvents evaporated under reduced pressure to approximately half-volume, and the aqueous residue was acidified with 5N hydrochloric acid and washed with ethyl acetate. The acid phase was then basified with solid potassium carbonate, and extracted into ethyl acetate, the organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the title compound (D36) as a pale yellow solid (3.4 g, 45%).

Workup

  1. customwater (1,360 ml) was degassed for 0.5 hr, by the passage of a stream of argon
  2. additionTetrakistriphenylphosphine palladium (0) (1.35 g) was added
  3. temperaturethe mixture was cooled
  4. customthe solvents evaporated under reduced pressure to approximately half-volume
  5. washwashed with ethyl acetate
  6. extractionextracted into ethyl acetate
  7. dry with materialthe organic phase was dried (Na2SO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e98fcf6d94e7492c983a954f23aeb359
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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