Reacción #1258670

Ecuación de reacción

2-bromo-4-pyridinecarboxylic acid

phenylboronic acid

potassium phosphate

→

2-phenylisonicotinic acid

Rendimiento 53.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed under vacuum/Ar
2. 2
   workup.ADDITIONA catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube
3. 3
   Otrothe mixture was degassed again
4. 4
   Otrothe tube was sealed
5. 5
   FiltraciónThe reaction mixture was filtered
6. 6
   Concentraciónthe filtrate was concentrated in-vacuo
7. 7
   workup.DISSOLUTIONthe residue was dissolved in water (10 mL)
8. 8
   workup.ADDITIONThe mixture was acidified to pH=6 with the addition of 1.0 N HCl
9. 9
   Filtraciónthe resulting precipitate was collected by filtration
10. 10
    Lavadorinsed with two portions of ice-cold water, and air
11. 11
    Otrodried

Procedimiento

A mixture of 2-bromo-4-pyridinecarboxylic acid (1.1 g, 5.45 mmol), phenylboronic acid (1.3 g, 10.9 mmol), 2.0 M potassium phosphate (aq) (8.2 mL, 16.34 mmol), and DMF (10 mL) in a 20 mL microwave tube was degassed under vacuum/Ar. A catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube, the mixture was degassed again, the tube was sealed, and the reaction was heated at 150° C. in the microwave for 30 min. The reaction mixture was filtered, the filtrate was concentrated in-vacuo, and the residue was dissolved in water (10 mL). The mixture was acidified to pH=6 with the addition of 1.0 N HCl, and the resulting precipitate was collected by filtration, rinsed with two portions of ice-cold water, and air dried to yield 575 mg of 2-phenylisonicotinic acid as an off-white solid. MS (ES+)=200 (M+H+).

Fuente