Reaktion #41071

Reaktionsgleichung

5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione

2-fluoro-5-chloropyridine-3-boronic acid

KF

→

title compound

Ausbeute 6.0%

5-(5-chloro-2-fluoro-3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochloride

Ausbeute 6.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed in a microwave oven
2. 2
   FiltrationThe mixture was filtered
3. 3
   SonstigeMeOH was evaporated
4. 4
   Sonstigethe crude partitioned between brine and ethyl acetate
5. 5
   TrocknenThe organic phase was dried (Na2SO4)
6. 6
   Sonstigeevaporated
7. 7
   Sonstigethe crude was purified by flash chromatography with ethyl acetate-NH4OH (0.5%)

Vorschrift

A mixture of 5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione (Prep 40, 150 mg, 0.3 mmol), 2-fluoro-5-chloropyridine-3-boronic acid (142 mg, 0.9 mmol), KF (157 mg, 2.7 mmol), and Pd(OAc)2 (20 mg) in degassed MeOH (4 ml) was placed in a microwave oven and warmed at 120° C. for 25 minutes. The mixture was filtered, MeOH was evaporated and the crude partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with ethyl acetate-NH4OH (0.5%) to give the title compound (10 mg, 6% yield).

Quelle