Reacción #67778

Ecuación de reacción

4-Bromo-2-methylaniline

3-fluoropyridine-4-carboxylic acid

LiHMDS

→

desired product

Rendimiento 70.0%

3-[(4-Bromo-2-methylphenyl)amino]isonicotinic acid

Rendimiento 70.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to ambient temperature
2. 2
   OtroAfter 24 h the reaction was quenched
3. 3
   workup.ADDITIONby adding a solution of HCl in dioxane (4.0M, 2.0 ml)
4. 4
   OtroThe volatiles were removed in vacuo
5. 5
   Otrothe crude material was purified by flash chromatography

Procedimiento

4-Bromo-2-methylaniline (186 mg, 1.00 mmol) and 3-fluoropyridine-4-carboxylic acid (141 mg, 1.00 mmol) were dissolved in dry THF (6.0 ml) under argon and the mixture was cooled to −78° C. A solution of LiHMDS (1.0M in THF, 3.5 ml) was added and the reaction mixture was allowed to warm to ambient temperature. After 24 h the reaction was quenched by adding a solution of HCl in dioxane (4.0M, 2.0 ml). The volatiles were removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 215 mg (701 μmol; 70% yield) of pure desired product.

Fuente