Reacción #339245

Ecuación de reacción

4-Bromo-2-bromomethyl-6-chlorobenzoic acid methyl ester

(4,4-difluorocyclohexyl)methylamine

K2CO3

→

title compound

Rendimiento 62.1%

5-Bromo-7-chloro-2-[(4,4-difluorocyclohexyl)methyl]isoindolin-1-one

Rendimiento 62.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was partitioned between ethyl acetate and water
2. 2
   Lavadothe organic layer was washed with brine
3. 3
   Secadodried over anhydrous Na2—SO4
4. 4
   OtroThe solvent was removed under reduced pressure
5. 5
   Otrothe product was purified by column chromatography (10-25% EtOAc/Hexanes)

Procedimiento

4-Bromo-2-bromomethyl-6-chlorobenzoic acid methyl ester (3.5 g, 9.35 mmol), (4,4-difluorocyclohexyl)methylamine (1.7 g, 11.39 mmol) and K2CO3 (3.15 g, 22.78 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2—SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford the title compound as a yellow foam (2.2 g, 45%), 1H NMR (300 MHz, CDCl3): 7.58 (s, 1H), 7.50 (s, 1H), 4.36 (s, 2H), 3.48 (d, 2H), 2.10-2.14 (m, 2H), 1.64-1.82 (m, 5H), 1.35-1.447 (m, 2H)

Fuente