Reacción #42552

Ecuación de reacción

N-[(1S,2R)-3-{[1-(3-bromophenyl)cyclopropyl]amino}-1-(3,5-difluorobenzyl)-2-hydroxypropyl]acetamide

3-methoxyphenylboronic acid

Cs2CO3

→

title compound

Rendimiento 31.4%

N-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[1-(3′-methoxy-1,1′-biphenyl-3-yl)cyclopropyl]amino}propyl)acetamide

Rendimiento 31.4%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine (10 mL×2)
2. 2
   SecadoThe organic layer was dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated under reduced pressure
5. 5
   OtroThe resulting residue was purified by column chromatography

Procedimiento

To a solution of N-[(1S,2R)-3-{[1-(3-bromophenyl)cyclopropyl]amino}-1-(3,5-difluorobenzyl)-2-hydroxypropyl]acetamide (0.030 g) in DMF (0.75 mL) was added 3-methoxyphenylboronic acid (0.030 g), Cs2CO3 (0.085 g) and Pd(Ph3P)4. The mixture was heated for 12 h at 90° C. The cooled solution was diluted with EtOAc (15 mL) and washed with brine (10 mL×2). The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting residue was purified by column chromatography to give 0.010 g of the title compound. ES+ found (M+H+):481.

Fuente