Reacción #161803

Ecuación de reacción

potassium carbonate

1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one dihydrochloride

(2-chloropyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

DIPEA

→

1-[4′-(5-fluoro-2,3-dihydroindole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1.2′]bipyridinyl-4-yl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one

Disolventes

water

N-methylpyrrolidone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred for a further 24 h at 130° C
2. 2
   Extracciónextracted with EtOAc (3×100 mL)
3. 3
   OtroThe combined organic phases were dried
4. 4
   Otroevaporated
5. 5
   Otrothe rotary evaporator
6. 6
   OtroThe residue was purified by preparative HPLC
7. 7
   Otroevaporated down i
8. 8
   OtroThe residue was triturated with 30 mL diethyl ether
9. 9
   Filtraciónfiltered
10. 10
    Otrodried in the air

Procedimiento

232 mg (0.8 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one dihydrochloride were added to 220 mg (0.80 mmol) (2-chloropyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.52 mL (3.00 mmol) DIPEA in 3.0 mL N-methylpyrrolidone. The reaction mixture was stirred for 6 h at 130° C. After 4 h 400 mg potassium carbonate were added and the reaction mixture was stirred for a further 24 h at 130° C. Then the mixture was poured onto 100 mL water and extracted with EtOAc (3×100 mL). The combined organic phases were dried and evaporated down using the rotary evaporator. The residue was purified by preparative HPLC. The product fractions were combined and evaporated down i. vac. The residue was triturated with 30 mL diethyl ether. The precipitated solid was suction filtered and dried in the air.

Fuente