Reaktion #41763

Reaktionsgleichung

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuum
8. 8
   Sonstigeto give brown solid
9. 9
   SonstigePurification on silica gel

Vorschrift

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.

Quelle