Réaction #42552

Équation de réaction

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

3-methoxyphenylboronic acid

Cs2CO3

→

title compound

Rendement 31.4%

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

Rendement 31.4%

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

1. 1
   Lavagewashed with brine (10 mL×2)
2. 2
   SéchageThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Autreevaporated under reduced pressure
5. 5
   AutreThe resulting residue was purified by column chromatography

Mode opératoire

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.

Source