Reacción #1957952

Ecuación de reacción

diethylether

6-[N-(2-Benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide

boron trichloride dimethyl sulphide

sodium bicarbonate

→

6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

Rendimiento 52.3%

Disolventes

methanol

Dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a pH of around 9
2. 2
   Otrothe organic and aqueous layers separated
3. 3
   Lavadothe aqueous layer washed with dichloromethane
4. 4
   LavadoThe combined organic extracts were then washed with brine
5. 5
   Otrodried
6. 6
   Otroevaporated
7. 7
   Otroto give a sticky solid
8. 8
   workup.WAITleft at ambient temperature overnight
9. 9
   FiltraciónThe resultant solid was filtered
10. 10
    Lavadowashed with diethylether
11. 11
    Otrosucked dry

Procedimiento

6-[N-(2-Benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide (3.24 g, 7.3 mmol) in dichloromethane (50 ml) was treated with boron trichloride dimethyl sulphide reagent (18.5 ml, 2M solution) in dichloromethane (37 mmol) and the solution stirred at ambient temperature for 6 days. The mixture was carefully treated with excess aqueous sodium bicarbonate solution to give a pH of around 9. Dichloromethane was added, the organic and aqueous layers separated and the aqueous layer washed with dichloromethane. The combined organic extracts were then washed with brine, dried and evaporated to give a sticky solid. This was treated with diethylether (30 ml) and methanol (3 ml) and left at ambient temperature overnight. The resultant solid was filtered, washed with diethylether and sucked dry to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide (1.34 g, 52%).

Fuente