5-bromo-3-methylpicolinonitrile

5-Bromo-3-methylpicolinonitrile (50) [0176] Copper(I) cyanide (21 g, 0.24 mol) was added to a solution of 2, 5-dibromo-3-methylpyridine (49, 60 g, 0.24 mol) in dry DMF (200 mL), and the mixture was heated at reflux for 2 h. After cooling to room temperature, water (1500 mL) was added to the mixture and the products were extracted with ethyl acetate (3×300 mL). The combined extracts were washed with water (3×300 mL), brine (300 mL), dried with sodium sulfate and evaporated to dryness. The brown oily residue was subjected to flash column chromatography (silica gel), eluting with chloroform, to yield 50 as a white solid (35 g, 74percent): mp 86-88° C. 1. Preparation of 5-bromo-3-methyl-2-cyanopyridine To a solution of 2, 5-dibromo-3-methylpyridine (5.0g, 19.9mmol) in N, N-dimethyl formamide (20mL) was added cuprous cyanide (1.8g, 20.0mmol). The resulting mixture was reacted at 120°C under stirring for 12hrs. The reaction mixture was cooled, to which water was added. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified with a silica-gel column chromatography (petroleum ether:ethyl acetate=5:1) to produce 2.4 g of the title compound as a white solid in a yield of 61.3percent.Step A To a solution of 2 5-dibromo-3-methylpyridine (5 g) in DMF (20 mL) was added cyanocopper (1.785 g) . The mixture was stirred at 120 overnight and then cooled to RT. The mixture was partitioned between EA (50 mL) and water (50 mL) . The organic layer was washed with brine (50 mL) dried over NaDescription 1325-Bromo-3-methylpicolinonitrile (D132)N;1To a solution of 2, 5-dibromo-3-methylpyridine (5 g) in DMF (20 mL) was added cyanocopper (1.785 g). The mixture was stirred at 120°C overnight and then cooled to RT. The mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was washed with brine(50 mL), dried over Na2SO4 and concentrated under vacuum to leave the crude, which was purifiedby column chromatography (silica gel, petroleum ether/EtOAc = 4:1) to afford the title compound(600 mg, 13.14 percent yield) as white solid. MS (ESI): C7H5BrN2 requires 195; found 196 [M+H].A mixture of 2, 5-dibromo-3-methyl-pyridine (2.58 mL), copper(I) cyanide (2.14 g) and N, N-dimethylformamide (20 mL) was stirred under a nitrogen stream at 170°C for 2 hr. In a solution containing 2, 5-dibromo-3-methylpyridine (5 g)Of DMF (20 mL)The solution was added with copper cyanide (1.785 g). The mixture was stirred overnight at 120 ° C, Cool to RT. The mixture was dissolved in ΕΑ (50 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dehydrated by Na2S04 and concentrated in vacuo. The resulting residue was purified by column chromatography (using ΕΑ: PE = 20percent> to give the title compound (600 mg) as a white solidExample 9.1: 5-bromo-3-methylpyridine-2-carbonitrile;

Molecular Weight:197.03
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes