Reacción #41763

Ecuación de reacción

dimethylformamide

5-fluoro-2-nitrophenylamine

Potassium bis(trimethylsilyl)amide

(3-hydroxyphenyl)-N-methylcarboxamide

Potassium carbonate

→

N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was then concentrated
2. 2
   Otropartitioned between ethyl acetate and water
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with brine
5. 5
   Otrodried
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuum
8. 8
   Otroto give brown solid
9. 9
   OtroPurification on silica gel

Procedimiento

The mixture containing 5-fluoro-2-nitrophenylamine (1 eq), Potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (3-hydroxyphenyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and stirred at 90° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel gave N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide. It was taken in methanol and hydrogenated with catalytic amount of 10% Pd/C to give {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide. MS: MH+=272.

Fuente