Potassium Carbonate → 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

Temperature

130 °C

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.

1. stirringthe reaction mixture was stirred for a further 24 h at 130° C
2. extractionextracted with EtOAc (3×100 mL)
3. customThe combined organic phases were dried
4. customevaporated
5. customthe rotary evaporator
6. customThe residue was purified by preparative HPLC
7. customevaporated down i
8. customThe residue was triturated with 30 mL diethyl ether
9. filtrationfiltered
10. customdried in the air

ORD record

ord-fc9cbcb666e14676a9a63819ea78cdfc

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829006B2