Reacción #57391

Ecuación de reacción

Na2CO3

tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

2-bromo-6-fluoro-pyridine

NEt3

→

N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

Rendimiento 30.2%

Disolventes

DMF

EA

EA

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe phases were separated
2. 2
   Extracciónthe aq. phase was extracted with EA
3. 3
   LavadoThe combined organic phases were washed with a 1M aq. Na2CO3 solution
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated under a vacuum

Procedimiento

500 mg (1.69 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158 part b) were dissolved together with 355 mg (2.02 mmol) of 2-bromo-6-fluoro-pyridine in DMF (20 ml). 2.4 ml (16.9 mmol) of NEt3, 32 mg (0.17 mmol) of copper(I) iodide and 119 mg (0.17 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with a 1M aq. Na2CO3 solution, dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (0.51 mmol, 30%) of N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (EA) of the group.

Fuente