Reaktion #70503

Reaktionsgleichung

heptane

4-methylbenzylamine

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

sodium carbonate

→

solid

Ausbeute 41.0%

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

Ausbeute 41.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in DCM
3. 3
   Waschenwashed with water and brine
4. 4
   TrocknenThe organic solution was dried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto afford a crude oil
7. 7
   SonstigeThe mixture was purified by flash chromatography on silica gel
8. 8
   Wascheneluting with 10-80% EtOAc

Vorschrift

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%).

Quelle