Réaction #955930

Équation de réaction

3,6-dichloropyridazine

NaH

pyridin-2-ylmethanol

→

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

Rendement 62.0%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source