Reacción #978522

Ecuación de reacción

2-Benzyl-4-chloro-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

2-Benzyl-4chloro-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

3,4-dimethylbenzeneboronic acid

CsF

→

desired compound

Rendimiento 56.0%

2-Benzyl-4-(3,4-dimethylphenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Rendimiento 56.0%

Disolventes

DME

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Extracciónextracted with ethyl acetate (100 mL)
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Otroevaporated in vacuo
6. 6
   OtroThe compound was purified on a silica gel column
7. 7
   Lavadoeluting with 30% ethyl acetate in pentanes

Procedimiento

2-Benzyl-4-chloro-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (150 mg, 0.4 mmol) prepared in Example 78 was dissolved in anhydrous DME (10 mL) and heated to reflux with 3,4-dimethylbenzeneboronic acid in presence of CsF (146 mg, 0.96 mmol) and tetrakis(triphenylphosphine)palladium (14 mg, 0.012 mmol) for 6 hours. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate (100 mL). The organic layer was washed with brine, dried over MgSO4, and evaporated in vacuo. The compound was purified on a silica gel column, eluting with 30% ethyl acetate in pentanes, providing the desired compound (yield: 100 mg, 56%). 1H NMR (300 MHz, CDCl3) δ 2.15, 2.20 (2s, 3H), 2.25, 2.30 (2s, 3H), 3.05, 3.08 (2s, 3H), 5.35, 5.40 (2s, 2H), 6.60-7.1, (m, 3H), 7.30-7.40 (m, 4H), 7.42-7.60 (m, 2H), 7.70-8, 02 (m, 4H). MS (DCI/NH3) m/z 445 (M+H)+. Anal. calc. for C26H24N2O3S.H2O: C, 67.51; H, 5.66; N, 6.05. Found: C, 67.45; H, 5.56; N, 5.85.

Fuente