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

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

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%).