Reacción #44397

Ecuación de reacción

1-bromo-2,3-dichloro-benzene

[1,4]diazepine-1-carboxylic acid tert-butylester

BINAP

→

title compound

1-(2,3-dichlorophenyl)-[1,4]diazepine

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for eight hours
2. 2
   Filtraciónfiltered
3. 3
   LavadoThe organic layer was washed with water
4. 4
   Otrodried
5. 5
   Otroevaporated in vacuo
6. 6
   OtroThe residue was purified by chromatography
7. 7
   Otrodeprotected at 10° C.
8. 8
   Filtraciónthe precipitate was filtered

Procedimiento

2.25 g (10 mmol) 1-bromo-2,3-dichloro-benzene was dissolved in dry toluene (50 ml), 2.3 (11 mmol) of [1,4]diazepine-1-carboxylic acid tert-butylester was added followed by 0.2 g BINAP (2,2-bis(diphenylphosphino)-1,1′-binaphtyl), 85 mg tris(dibenzylideneacetone)dipalladium(0) and 1.2 g (12 mmol) sodium-tert-butoxyde. The reaction mixture was refluxed for eight hours and filtered. The organic layer was washed with water, dried and evaporated in vacuo. The residue was purified by chromatography and deprotected at 10° C. using 20 ml ethylacetate saturated with gaseous hydrochloric acid, the precipitate was filtered giving 2.1 g (yield: 75%) hydrochloride salt of the title compound, melting at 182-3° C.

Fuente