Reaktion #422965

Reaktionsgleichung

(1R,2R)-diaminomethylcyclohexane

10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one

4-iodotoluene

potassium carbonate

→

10-methylene-8-(pyridin-3-yl)-2-p-tolyl-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe system was purged with argon
2. 2
   Sonstigethe tube was sealed
3. 3
   workup.ADDITIONThe reaction mixture was diluted with dichloromethane
4. 4
   Filtrationfiltered through a pad of celite
5. 5
   EinengenThe filtrate was concentrated
6. 6
   Sonstigepartitioned between dichloromethane and water
7. 7
   SonstigeThe aqueous phase was separated
8. 8
   Extraktionextracted with dichloromethane
9. 9
   WaschenThe combined organic phases were washed with brine
10. 10
    Trocknendried over anhydrous sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated

Vorschrift

A resealable tube was charged with (1R,2R)-diaminomethylcyclohexane (9.77 mg, 0.069 mmol), copper(I) iodide (8.72 mg, 0.046 mmol), 10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one (0.066 g, 0.229 mmol), 4-iodotoluene (0.055 g, 0.252 mmol), potassium carbonate (0.063 g, 0.458 mmol), and DMSO (2.5 mL). The system was purged with argon and the tube was sealed. The mixture stirred in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 2 h. The reaction mixture was diluted with dichloromethane and filtered through a pad of celite. The filtrate was concentrated and partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 10-methylene-8-(pyridin-3-yl)-2-p-tolyl-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one. MS m/z=379.0 [M+H]+. Calcd for C25H18N2O2: 378.4.

Quelle