2-BROMO-6-HYDRAZINYLPYRIDINE

Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (50-60percent) was added. The mixture was heated in a sand-bath at 115° C. for 18 h. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93percent).Step A Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (~50-60 percent) was added. The mixture was heated in a sand-bath at ~115 °C for 18 h. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93 percent). Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (50-60percent) was added. The mixture was heated in a sand-bath at 115° C. for 18 h. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93percent).Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 ml_, 97.6 mmol) in water (-50-60 percent) was added. The mixture was heated in a sand-bath at ~115 °C for 18 hours. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93 percent). (0761) Step A (0762) Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (50-60percent) was added. The mixture was heated in a sand-bath at 115° C. for 18 hours. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93percent). (0763) Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazinehydrate (10 mL, 97.6 mmol) in water (∼50-60 percent) was added. The mixture was heated in a sand-bath at ∼115°C for 18 hours. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/nheptane(60/40) to afford the title compound as an off-white solid (3.05 g, 93 percent). 1H-NMR (400 MHz, CDCl3): δ = 7.33 (t, 1 H), 6.83 (d, 1 H), 6.67 (d, 1 H), 6.00 (br-s, 1 H), 3.33-3.00 (br-s, 2H)Commercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (-50-60 percent) was added. The mixture was heated in a sand-bath at -1 15 °C for 18 hours. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93 percent). (0163) H-NMR (400 MHz, CDCICommercially available 2, 6-dibromopyridine (4.12 g, 16.6 mmol) was suspended in ethanol (40 mL) and hydrazine hydrate (10 mL, 97.6 mmol) in water (-50-60 percent) was added. The mixture was heated in a sand-bath at -115 °C for 18 hours. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) to afford the title compound as an off-white solid (3.05 g, 93 percent). (0184) H-NMR (400 MHz, CDCIHydrazine (27 mL, 83 mmol) was added to 2, 6-dibromopyridine (20 g, 84 mmol), and the resulting suspension was heated at 70° C. for 30 min. The solution was cooled to 50° C. and diluted with HHydrazine (27 mL, 83 mmol) was added to 2, 6-dibromopyridine (20 g, 84 mmol), and the resulting suspension was heated at 70° C. for 30 min.A mixture of 2, 6-dibromopyridine (Aldrich; 2.37g, 0.01 mol) and hydrazine hydrate (0.53 ml) in ethanol (50 ml) was heated at 802, 6-dibromopyridine 2a (2.37 g, 10.0 mmol), hydrazine hydrate (20.0 mmol) and 20 mL of n-butanol was stirred at 120 ° C for 12 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The solid was washed three times with water (5 mL) and ether (5 mL) and vacuum dried at 50 ° C for 2 hours to give brown solid 4a as the target product (1.25 g, 67percent yield)

Molecular Weight:188.03
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:186.97451
Monoisotopic Mass:186.97451
Topological Polar Surface Area:50.9
Heavy Atom Count:9
Complexity:88.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes