6-bromo-4-chlorocinnoline

Thionyl chloride (3 mL) and N, N-dimethylformamide (30 μL) were added to 6-bromocinnolin-4 (1 H) -one (300 mg, 1.33 mmol) and the mixture was heated under reflux for 30 minutes. The reaction solution was concentrated, Saturated multilayer water was added to the obtained residue, And extracted with ethyl acetate. The organic layer was washed with saturated brine, After drying over anhydrous magnesium sulfate, filtration, The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate)To give the title compound (288 mg, 89percent). Yellow solid6-l3romo-4-chlorocinnoline (8a) In a flame dried250 mE round bottom flask was added 6-bromocinnolin-4 (1H)-one (1.00 g, 4.44 mmol), anhydrous tetrahydrofuran (45 mE), and phosphorus oxychloride (1.25 mE, 13.41 mmol). The mixture was refluxed for 1 hour at which point a deep greenlblue solution had resulted. The solution was cooled to 0° C. and was quenched by the dropwise addition of sat. aq. NaHCO3 (70 mE). The mixture was allowed to warm to room temperature and stir for an additional 1 hout Water (50 mE) was added and the mixture was extracted with dichloromethane (3x100 mE). The combined organic layers were washed with sat. aq. NaHCO3 (50 mE), washedwith brine (50 mE), dried over Na2SO4, and concentrated on to silica, and purified by flash column chromatography using a gradient of 1-5percent methanol in dichloromethane to yield an inseparable10:1 mixture of 8a and 8b as a brown solid in 85percent yield. ‘H NMR (500 MHz, CDC13) ö 9.36 (s, 1H), 8.43 (d, J=8.8 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 7.98 (dd, J=9.3, 2.0 Hz, 1H). ECMS found 242.9/199.0 [M+H].

Molecular Weight:243.49
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Exact Mass:241.92464
Monoisotopic Mass:241.92464
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes