Réaction #2286325

Équation de réaction

sodium cyanide

sulfuric acid

6-(2,6-dibromo-4-chloromethyl-benzyl)-4-isopropyl-pyridazin-3-one

6-(2,6-Dibromo-4-chloromethyl-benzyl)-4-isopropyl-pyridazin-3-one

→

[3,5-dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

Rendement 67.6%

[3,5-Dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

Rendement 67.6%

Solvants

dimethyl sulfoxide

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONan addition
2. 2
   Lavagerinse of dimethyl sulfoxide (3.0 mL)
3. 3
   TempératureAt this time, the reaction was heated to 60° C. for 1 h
4. 4
   Températurewas cooled to 25° C
5. 5
   workup.ADDITIONThe mixture was poured onto a mixture of ice
6. 6
   ExtractionThis mixture was extracted into ethyl acetate (3×50 mL)
7. 7
   LavageThe combined organics were washed with a saturated aqueous sodium chloride solution (1×50 mL)
8. 8
   Séchagedried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated under vacuum

Mode opératoire

A suspension of sodium cyanide (279 mg, 5.69 mmol) in dimethyl sulfoxide (2.0 mL) was treated with concentrated sulfuric acid (0.10 mL), 6-(2,6-dibromo-4-chloromethyl-benzyl)-4-isopropyl-pyridazin-3-one (62) (346 mg, 0.79 mmol) and an addition rinse of dimethyl sulfoxide (3.0 mL). The reaction was stirred at 25° C. for 5 min and at 40° C. for 1 h. At this time, the reaction was heated to 60° C. for 1 h and then was cooled to 25° C. The mixture was poured onto a mixture of ice and a saturated aqueous sodium bicarbonate solution (50 mL). This mixture was extracted into ethyl acetate (3×50 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1:2 hexanes/ethyl acetate) afforded [3,5-dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile (63) (227 mg, 67%) as a light orange solid; LRMS for C16H15Br2N3O (M+H) at m/z=424. Molecular Weight=425.1255; Exact Mass=422.9582

Source