Reaktion #2294781

Reaktionsgleichung

4-trifluoromethylphenyl-boronic acid

sodium carbonate

7-(benzene-sulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one

→

3-(benzenesulfonyl)-7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)-phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one

Ausbeute 103.2%

3-(Benzenesulfonyl)-7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one

Ausbeute 103.2%

Lösungsmittel

water EtOAc

DME

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigethe phases separated
3. 3
   TrocknenThe organic layer was dried (Na2SO4)
4. 4
   Sonstigethe solvent evaporated
5. 5
   Sonstigeto afford a light brown solid
6. 6
   SonstigeThis was purified
7. 7
   Wascheneluting with 0 to 10% MeOH/EtOAc

Vorschrift

PdCl2(Ph3P)2 (128.4 mg, 0.1800 mmol) was added to a degassed mixture of 4-trifluoromethylphenyl-boronic acid (365.03 mg, 1.92 mmol), sodium carbonate (582.01 mg, 5.49 mmol) and 7-(benzene-sulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 12) (850 mg, 1.83 mmol) in DME (12 mL) and water (4 mL) under N2 in a microwave vial and the reaction was heated in the microwave at 120° C. for 1 hour. The mixture was diluted with water/EtOAc, filtered, and the phases separated. The organic layer was dried (Na2SO4) and the solvent evaporated to afford a light brown solid. This was purified using a Biotage SP4, 25 g SNAP cartridge, eluting with 0 to 10% MeOH/EtOAc to afford the 3-(benzenesulfonyl)-7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)-phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one (D16) (1 g, 1.8883 mmol) as an off-white solid (with traces of impurities);

Quelle