Reacción #84202

Ecuación de reacción

ammonium chloride

5-methoxy-1H-indole

methylmagnesium bromide

1-naphthoylchloride

→

5-methoxy-3-(1-naphthoyl)-1H-indole

Rendimiento 75.0%

Disolventes

diethyl ether

diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was then cooled at 0° C. and to this solution
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturawas warmed up at room temperature
4. 4
   workup.STIRRINGstirred for 2 h
5. 5
   workup.STIRRINGstirred overnight
6. 6
   OtroThe white solid formed
7. 7
   Filtraciónwas filtered
8. 8
   Lavadowashed by ether
9. 9
   Otrodried under high vacuum

Procedimiento

To a cooled solution at 0° C. of 5-methoxy-1H-indole 3 (7.4 g, 50 mmol) in diethyl ether (150 ml) under nitrogen was added dropwise a solution of methylmagnesium bromide (3M) in diethyl ether (17.5 ml) and the mixture was stirred for 2 h at room temperature. The solution was then cooled at 0° C. and to this solution was added a solution of 1-naphthoylchloride (9.5 g, 50 mmol) in diethyl ether (100 ml) dropwise over a period of 15 min. After the addition was completed the solution was warmed up at room temperature and stirred for 2 h followed by slow addition of saturated ammonium chloride solution (375 ml) and stirred overnight. The white solid formed was filtered, washed by ether and dried under high vacuum to give 5-methoxy-3-(1-naphthoyl)-1H-indole 4 (11.3 g, 75%).

Fuente