Bromine → 1-Benzyl-3-bromo-7-(4-fluorobenzyloxy)-2-methylpyrrolo[2,3-d]pyridazine
Reaktionsgleichung
[Br:1]Br.[CH2:3]([N:10]1[C:14]2=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:16]=[N:17][CH:18]=[C:13]2[CH:12]=[C:11]1[CH3:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCl>[CH2:3]([N:10]1[C:14]2=[C:15]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[N:16]=[N:17][CH:18]=[C:13]2[C:12]([Br:1])=[C:11]1[CH3:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 180 μl (3.5 mmol) of bromine in 7 ml of anhydrous dichloromethane is added dropwise at 0° C. to a solution of 910 mg (2.6 mmol) of 1-benzyl-7-(4-fluorobenzyloxy)-2-methylpyrrolo[2,3-d]pyridazine in 15 ml of anhydrous dichloromethane in the course of 30 min. The solution is kept at 0° C. for a further 1 h, then treated with 50 ml of ice-water and extracted. The organic phase is separated off, washed with 3×25 ml of water, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (eluent: ethyl acetate). The fractions of Rf=0.6 are concentrated and crystallized from diisopropyl ether/cyclohexane. 880 mg (79%) of the title compound are isolated. M.p.: 128°-130° C.