Potassium Phosphate, Tribasic → 5-Methyl-2-isopropyloxy-4-(pyridine-4-YL)-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

4-Pyridineboronic acid (147 mg, 1.20 mmol, 1.1 equiv.) was dissolved in a 2:1 v/v mixture of dioxane and H2O (15 mL) and N2 was bubbled through for 5 minutes. Tris(dibenzylidene acetone)dipalladium (0) (100 mg, 0.109 mmol, 0.1 equiv.), 2-dicyclohexylphosphine-2′-6′-dimethoxy biphenyl (112 mg, 0.272 mmol, 0.25 equiv.), 1-chloro-5-isopropoxy-2-methyl-4-nitro-benzene (250 mg, 1.09 mmol, 1.0 equiv.) and K3PO4 (462 mg, 2.18 mmol, 2.0 equiv.) were added under a N2 blanket. The reaction vessel was sealed and heated with microwave irradiation to 150° C. for 20 minutes. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed with 1N aqueous NaOH (twice). The organic layer was then dried over Na2SO4 and filtered. After concentration, the crude product was purified by silica gel chromatography (gradient from hexanes to 30% ethyl acetate in hexanes) to give 4-(5-Isopropoxy-2-methyl-4-nitro-phenyl)-pyridine as a brown solid: ESMS m/z 273.1 (M+H+).

Provenance & Evidence