Réaction #70503

Équation de réaction

heptane

4-methylbenzylamine

4,5-bis(bromomethyl)-3,6-dichloropyridazine

sodium carbonate

→

solid

Rendement 41.0%

1,4-dichloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyridazine

Rendement 41.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in DCM
3. 3
   Lavagewashed with water and brine
4. 4
   SéchageThe organic solution was dried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   Autreto afford a crude oil
7. 7
   AutreThe mixture was purified by flash chromatography on silica gel
8. 8
   Lavageeluting with 10-80% EtOAc

Mode opératoire

To a suspension of 4,5-bis(bromomethyl)-3,6-dichloropyridazine (800 mg, 2.39 mmol) in 40 mL anhydrous THF was added with sodium carbonate (507 mg, 4.78 mmol) and tetrabutylammonium iodide (88.3 mg, 0.24 mmol). The reaction mixture was added with 4-methylbenzylamine (0.31 mL, 2.39 mmol) in 20 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 8 h and concentrated. The crude material was dissolved in DCM and washed with water and brine. The organic solution was dried over Na2SO4 and concentrated to afford a crude oil. The mixture was purified by flash chromatography on silica gel, eluting with 10-80% EtOAc:heptane to afford a off-white solid (300 mg, yield: 41%).

Source