Réaction #66301

Équation de réaction

4,4′-(phenylphosphinidene)bisbenzenesulfonic acid dipotassium hydrate

tert-Butyl (1E,4E)-8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate

sodium carbonate

4-hydroxyphenylboronic acid

→

tert-butyl (1E,4E)-4-(dipropylcarbamoyl)-8-(4-hydroxyphenyl)-3H-benzo[b]azepin-2-ylcarbamate

Rendement 41.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Autrethis mixture was purged with Argon for 5 minutes
2. 2
   workup.ADDITIONThe mixture was then diluted with citric acid
3. 3
   Extractionextracted with EtOAc (2×)
4. 4
   Lavageextracts washed with saturated sodium carbonate solution
5. 5
   Séchagedried over sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

tert-Butyl (1E,4E)-8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate (0.095 g, 0.205 mmol), 4-hydroxyphenylboronic acid (0.040 g, 0.286 mmol), Pd(OAc)2 (0.0045 g, 0.020 mmol), 4,4′-(phenylphosphinidene)bisbenzenesulfonic acid dipotassium hydrate (0.022 g, 0.041 mmol), 2M sodium carbonate solution (0.307 mls, 0.614 mmol) were combined in 2 mls of ethanol and this mixture was purged with Argon for 5 minutes and then warmed to 65° C. under argon for 1.5 hours. The mixture was then diluted with citric acid, extracted with EtOAc (2×), extracts washed with saturated sodium carbonate solution, dried over sodium sulfate and concentrated under reduced pressure. Flash 40 Biotage (40S cartridge, 30% EtOAc/Hexane) afforded 0.040 g of tert-butyl (1E,4E)-4-(dipropylcarbamoyl)-8-(4-hydroxyphenyl)-3H-benzo[b]azepin-2-ylcarbamate (41%). m/z (APCI-pos) M+1=478.0.

Source