Reacción #968900

Ecuación de reacción

sodium carbonate

methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

6-bromopyridin-3-amine

→

title compound

Rendimiento 131.0%

methyl2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Rendimiento 131.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 120° C.
2. 2
   Otrofor 50 minutes
3. 3
   ConcentraciónThe resulting mixture was concentrated to dryness
4. 4
   Secadothe slurry was dried over sodium sulfate
5. 5
   Filtraciónfiltered through a pad of celite
6. 6
   ConcentraciónThe filtrate was concentrated
7. 7
   Otropurified by column chromatography

Procedimiento

To a microwave vial containing methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (100 mg, 0.26 mmol), 6-bromopyridin-3-amine (49 mg, 0.28 mmol) and Pd2(PPh3)4 (60 mg, 0.05 mmol) was added 1,4-dioxane (1.3 ml) at room temperature. 2N sodium carbonate (0.39 ml, 0.78 mmol) was added and the mixture was subjected to microwave radiation at 120° C. for 50 minutes. The resulting mixture was concentrated to dryness and taken up in EtOAc, the slurry was dried over sodium sulfate and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography to afford the title compound (120 mg, 65% yield). LC/MS, ESI-MS(+): 353.4, RT: 1.12 (Condition E).

Fuente