Reacción #11522

Ecuación de reacción

(Aminocarbonyl)amino-5-bromothiophene-2-carboxamide

1-benzothien-3-ylboronic acid

→

(Aminocarbonyl)amino-5-(1-benzothien-3-yl)thiophene-2-carboxamide

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrosaturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon
2. 2
   workup.ADDITIONTetrakis(triphenylphosphine)-palladium (95 mg) was added
3. 3
   Temperaturathe mixture was heated
4. 4
   Temperaturaat reflux
5. 5
   Temperaturato cool
6. 6
   workup.STIRRINGstirred at room temperature overnight
7. 7
   FiltraciónThe solution was filtered
8. 8
   Lavadowashed through with 1,2-dimethoxyethane and water
9. 9
   ConcentraciónThe filtrate was concentrated in vacuo
10. 10
    FiltraciónThe solid product was collected by filtration
11. 11
    Lavadowashed with dichloromethane, water, diethyl ether
12. 12
    Otrodried (226 mg)

Procedimiento

3-[(Aminocarbonyl)amino-5-bromothiophene-2-carboxamide (0.222 g) and 1-benzothien-3-ylboronic acid (0.449 g) were sonicated in 1,2-dimethoxyethane (15 ml) and saturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon. Tetrakis(triphenylphosphine)-palladium (95 mg) was added and the mixture was heated at reflux with stirring for 4.5 h, then allowed to cool and stirred at room temperature overnight. The solution was filtered and washed through with 1,2-dimethoxyethane and water. The filtrate was concentrated in vacuo and taken up in dichloromethane (20 ml) and saturated aqueous sodium hydrogen carbonate solution (20 ml). The solid product was collected by filtration, washed with dichloromethane, water, diethyl ether and dried (226 mg).

Fuente