Reacción #42469

Ecuación de reacción

methyl 3,5-dibromo-4-methoxybenzoate

BINAP

cesium carbonate

butylamine

→

title compound

Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed overnight
2. 2
   TemperaturaThe mixture was cooled to room temperature
3. 3
   Filtraciónfiltered through diatomaceous earth
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

Procedimiento

To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.

Fuente