Reacción #955930

Ecuación de reacción

3,6-dichloropyridazine

NaH

pyridin-2-ylmethanol

→

3-chloro-6-(pyridin-2-ylmethoxy)pyridazine

Rendimiento 62.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at 55° C. for 4 hours
2. 2
   OtroThe reaction was quenched with water and sat. NaHCO3
3. 3
   workup.ADDITIONwas added
4. 4
   ExtracciónThe product was then extracted with EtOAc
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe residue was purified on silica gel(Eluent: 80% EtOAc in hexanes)

Procedimiento

To a solution of NaH (1.44 g, 36 mmol, 60% in mineral oil) in THF (15 mL) was added pyridin-2-ylmethanol (1.16 ml, 12 mmol) and the mixture was stirred for 30 min at rt. Then 3,6-dichloropyridazine (1.79 g, 14 mmol) was added and the mixture was stirred at 55° C. for 4 hours. The reaction was quenched with water and sat. NaHCO3 was added. The product was then extracted with EtOAc, dried over MgSO4 filtered and evaporated. The residue was purified on silica gel(Eluent: 80% EtOAc in hexanes) to give 3-chloro-6-(pyridin-2-ylmethoxy)pyridazine as a white solid (1.64 g, 62%). 1H NMR (300 MHz, dMSO): δ 5.57 (s, 2H), 7.35-7.38 (m, 1H), 7.48-7.54 (m, 2H), 7.82-7.88 (m, 2H), 8.57-8.59 (dd, 1H); MS (M+H, 222).

Fuente