Reacción #710941

Ecuación de reacción

Et2O

K2CO3

(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl)(morpholino)methanone

3-chlorobenzyl bromide

→

[3-(4-Chlorophenyl)-1-[(3-chlorophenyl)-methyl]-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-morpholin-4-yl-methanone

Disolventes

H2O

MeCN

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas lowered to room temperature
2. 2
   Otroto result in a clear two phase system
3. 3
   OtroThe phases were separated
4. 4
   Lavadothe organic phase was washed with brine
5. 5
   SecadoDrying (Na2SO4)
6. 6
   Concentraciónwas followed by concentration in vacuo
7. 7
   workup.DISSOLUTIONThe residue was dissolved in MeCN (30 mL)
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroproviding 96 mg (90%) of SC-25 as a fluffy white solid

Procedimiento

(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl)(morpholino)methanone (80 mg, 0.215 mmol) was dissolved in dry MeCN (5 mL). The solution was mixed with K2CO3 (59 mg, 0.429 mmol), followed by addition of 3-chlorobenzyl bromide (31 μL, 0.236 mmol). The reaction mixture was stirred vigorously at 80° C. overnight. The temperature was lowered to room temperature; the reaction mixture was combined with a few lumps of ice, Et2O (50 mL) and H2O (10 mL) to result in a clear two phase system. The phases were separated; the organic phase was washed with brine. Drying (Na2SO4) was followed by concentration in vacuo. The residue was dissolved in MeCN (30 mL), concentrated in vacuo and used for preparative TLC (silica, heptane/EtOAc, 5:1), providing 96 mg (90%) of SC-25 as a fluffy white solid.

Fuente