Reacción #71546

Ecuación de reacción

2-chloro-5-iodopyridin-4-amine

Compound 11

2-chloro-5-iodopyridin-4-amine

3-methyl-1-butyne

→

title compound

2-Chloro-5-(3-methylbut-1-ynyl)pyridin-4-amine

Disolventes

Et3N

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas quenched with H2O
2. 2
   Extracciónextracted with EtOAc (Δ2)
3. 3
   LavadoThe combined organic layer was washed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Procedimiento

To a solution of 2-chloro-5-iodopyridin-4-amine (Compound 11, 2.55 g, 10.0 mmol) in Et3N (35 ml) was added Pd(PPh3)2Cl2 (70 mg, 0.10 mmol), CuI (19 mg, 0.10 mmol), and 3-methyl-1-butyne (1.2 ml, 12 mmol). The reaction was stirred at room temperature for 20 h and was quenched with H2O, extracted with EtOAc (Δ2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as an off-white solid.

Fuente