Reaktion #2440754

Reaktionsgleichung

5-Chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one

exo-2-bromonorbornane

Cs2CO3

2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine

→

1-Bicyclo[2.2.1]hept-2-yl-5-chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one

Ausbeute 30.0%

2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine

Ausbeute 9.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter filtration
2. 2
   workup.ADDITIONthe filtrate was diluted with EtOAc
3. 3
   Waschenwashed with water
4. 4
   EinengenThe organic phase was concentrated
5. 5
   workup.DISSOLUTIONthe residue was dissolved in a minimum amount of DCM
6. 6
   Sonstigesubjected to silica gel column purification

Vorschrift

1-Bicyclo[2.2.1]hept-2-yl-5-chloro-3-p-tolyl-13-dihydro-imidazo[4,5-b]pyridine-2-one (38) and 2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine (39). A mixture of 5-Chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one (52 mg, 0.2 mmol), exo-2-bromonorbornane (103 μL, 0.8 mmol) and Cs2CO3 (195 mg, 0.6 mmol) in 1.5 mL DMF was heated in microwave at 200° C. for 20 min. After filtration, the filtrate was diluted with EtOAc, washed with water. The organic phase was concentrated, the residue was dissolved in a minimum amount of DCM, and subjected to silica gel column purification to give 21.2 mg (yield: 30%) 1-Bicyclo[2.2.1]hept-2-yl-5-chloro-3-p-tolyl-1,3-dihydro-imidazo[4,5-b]pyridine-2-one (Rf=0.60 in DCM) and 6.2 mg (yield: 9%) 2-(Bicyclo[2.2.1]hept-2-yloxy)-5-chloro-3-p-tolyl-3H-imidazo[4,5-b]pyridine (Rf=0.49 in DCM). Calculated mass=353. Observed mass=354.

Quelle