Реакция #70503

Уравнение реакции

heptane

4-methylbenzylamine

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

sodium carbonate

→

solid

Выход 41.0%

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

Выход 41.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in DCM
3. 3
   Промывкаwashed with water and brine
4. 4
   СушкаThe organic solution was dried over Na2SO4
5. 5
   Концентрированиеconcentrated
6. 6
   Другоеto afford a crude oil
7. 7
   ДругоеThe mixture was purified by flash chromatography on silica gel
8. 8
   Промывкаeluting with 10-80% EtOAc

Методика

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%).

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