반응 #161803

반응 방정식

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

용매

water

N-methylpyrrolidone

반응 조건

후처리

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

실험 절차

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.

출처