Reaction #161869

Reaction equation

1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one

(2,6-dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

DIPEA

→

1-[6′-chloro-4′-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Solvents

DMF

Conditions

Workup

1. 1
   OtherThen the reaction mixture was evaporated down
2. 2
   workup.ADDITIONthe residue was mixed with water
3. 3
   Filtrationfiltered
4. 4
   workup.STIRRINGstirred with diisopropylether and isopropanol and suction
5. 5
   Filtrationfiltered again
6. 6
   DryingAfter drying the crude product
7. 7
   Otherwas purified by preparative HPLC-MS
8. 8
   Otherfreeze-dried

Procedure

0.74 g (3.4 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 1.0 g (3.2 mmol) (2,6-dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.65 mL (3.8 mmol) DIPEA in 10 mL DMF were stirred for 2 h at RT. Then the reaction mixture was evaporated down, the residue was mixed with water and stirred for 30 min at RT. The precipitated solid was suction filtered, stirred with diisopropylether and isopropanol and suction filtered again. After drying the crude product was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Source