Reaktion #74135

Reaktionsgleichung

4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide

tert-butylamine

p-toluensulfonic anhydride

→

title compound

Ausbeute 75.0%

N-tert-butyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridin-2-amine

Ausbeute 75.0%

Lösungsmittel

trifluoromethylbenzene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeAt 0° C
3. 3
   Sonstigewas removed under reduced pressure
4. 4
   Sonstigethe residue partitioned between dichloromethane and water
5. 5
   Trocknenthe organic layer dried over sodium sulphate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe crude was then purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 19/1)

Vorschrift

580 mg (1.44 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide were suspended in a mixture of 16 ml of trifluoromethylbenzene and 4 ml of dry dichloromethane and 756 μl of tert-butylamine were added. At 0° C. 936 mg (7.2 mmol) of p-toluensulfonic anhydride were added. After 6 hours under stirring in the same conditions the solvent was removed under reduced pressure, the residue partitioned between dichloromethane and water, the organic layer dried over sodium sulphate and evaporated. The crude was then purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 19/1), giving 500 mg (75%) of the title compound.

Quelle