Reacción #41718

Ecuación de reacción

4-amino-3-nitrophenol

potassium bis(trimethylsilyl)amide

(4-chloro(2-pyridyl))-N-methylcarboxamide

potassium carbonate

→

4-[(4-amino-3-nitrophenyl)oxy]-N-methylpyridine-2-carboxamide

Disolventes

dimethylformamide

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 (2% triethyl amine/50% ethyl acetate in hexane)

Procedimiento

A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (4-chloro(2-pyridyl))-N-methylcarboxamide (1 eq) and potassium carbonate (1.2 eq) and stirred at 90° C. for 3 days. 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 (2% triethyl amine/50% ethyl acetate in hexane) gave 4-[(4-amino-3-nitrophenyl)oxy]-N-methylpyridine-2-carboxamide as an orange solid. The product gave satisfactory NMR. HPLC, 3.39 min; MS: MH+=289.

Fuente