Reacción #2439974

Ecuación de reacción

Thiophene-2-carbonyl chloride

6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

→

Thiophene-2-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

Rendimiento 64.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 3 h
2. 2
   OtroThe room temperature reaction mixture
3. 3
   Concentraciónwas concentrated in vacuo
4. 4
   workup.DISSOLUTIONthe crude residue was dissolved in EtOH (5 mL)
5. 5
   workup.ADDITIONThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
6. 6
   Otroyielding a tan precipitate
7. 7
   FiltraciónThe tan solids were filtered

Procedimiento

A dry 25 mL flask was charged with Thiophene-2-carbonyl chloride (0.756 g, 5.16 mmol) and THF (10 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 15, 1.02 g, 3.98 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford the pure Thiophene-2-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.924 g, 2.53 mmol, 64%).

Fuente