Reacción #42305

Ecuación de reacción

methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

(Trimethylsilyl)acetylene

→

methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate

Rendimiento 111.3%

Disolventes

triethylamine

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated to reflux
2. 2
   Temperaturacooled to 20-25 degrees
3. 3
   Extracciónextracted with chloroform (3×15 mL)
4. 4
   LavadoThe combined organic extracts are washed with saline (20 mL)
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

A mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, 200 mg, 0.58 mmol), PdCl2(Ph3P)2 (16 mg, 0.03 mol %) and copper (I) iodide (6 mg, 0.05 mol %) in triethylamine (1.2 mL) is heated to reflux. (Trimethylsilyl)acetylene (100 microliter, 0.7 mmol) is added, and the mixture stirred for 3 hours, cooled to 20-25 degrees, diluted with water (20 mL), and extracted with chloroform (3×15 mL). The combined organic extracts are washed with saline (20 mL), dried over sodium sulfate and concentrated under reduced pressure to give methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate (XXXII, 185.5 mg), NMR (300 MHz, CDCl3): δ 7.95, 7.75, 7.43, 3.74, 3.25, 2.95, 1.49, 1.34, 0.79, 0.56 and 0.06.

Fuente