反应详情

温度

90 °C

To a deoxygenated solution of methyl 2-chloro-5-iodonicotinate (1-1, 2.01 g, 6.72 mmol, 1 equiv) and 3,5-dimethylphenylboronic acid (1.01 g, 6.72 mmol. 1.00 equiv) in dioxane (250 mL) was added tetrakis(triphenylphosphine)palladium(0) (155 mg, 0.134 mmol) and 2 N aqueous sodium bicarbonate solution (16.8 mL, 33.6 mmol, 5.00 equiv) and the reaction mixture was heated at 90° C. for 48 hours. The reaction mixture was allowed to cool to 23° C., then partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate solution (500 mL). The aqueous layer was filtered and acidified to pH 2 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration washed with water (2×100 mL) and air dried to afford 2-chloro-5-(3,5-dimethylphenyl)nicotinic acid (1-2) as an off white solid. LRMS m/z (M+H) 262.3 found, 262.1 required.

1. temperatureto cool to 23° C.
2. custompartitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate solution (500 mL)
3. filtrationThe aqueous layer was filtered
4. filtrationThe resulting precipitate was collected by filtration
5. washwashed with water (2×100 mL) and air
6. customdried