2-Bromo-3-(bromomethyl)pyridine

This intermediate was generated by a modified procedure based on thatdisclosed in Rebek, J., et al., I Am. Chem. Soc., 107, 7487 (1985)). A three-neckround bottom flask with a stir bar was flame dried, cooled under vacuum and purged with N2. To the flask were added 2-bromo-3-methylpyndine (5.2 mL, 29.1 mmol), N-bromosuccinimide (5.5 g, 32.0 mmol), and degassed benzene (126 mL). The flask was fitted with a condenser, heated to 40 °C and AIBN (0.24 g, 1.5 mmol) was addedin several portions. The reaction was irradiated using a sun lamp as it was stirred at40 °C. The reaction was monitored using TLC and HPLC and was stopped after 80percentconversion of the pyridine reagent (approximately 8 hrs). The reaction wasconcentrated under reduced pressure, then redissolved in 4:1 DCM/EtOAc (120 mL)and extracted once with 50 mL of a saturated solution of NaHCO3(aq), water and asaturated solution of NaCl(aq). The organic phase was dried over anhydrous sodiumsulphate, filtered and concentrated. Upon standing the residue could not be fully redissolved in DCM and the resultant suspension was filtered to remove the insoluble solid. The filtrate was concentrated to near dryness and the residue was purified by normal phase flash chromatography (EtOAc/Hexanes) to give the title compound I-i(3.0 g, 11.9 mmol, 41percent) as a yellow solid. ‘H NMR (400 MHz, CDC13) ö 8.33 (1H, dd, J5, 2 Hz), 7.78 (1H, dd, J7, 2 Hz), 7.28 (1H, dd, J=5, 4 Hz), 4.57 (2H, s), MS (LC/MS) m/z observed 249.97, expected 249.89 [M+HjThis intermediate was generated by a modified procedure based on that disclosed in Rebek, J., et al., J Am. Chem. Soc., 107, 7487 (1985)). A three-neck round bottom flask with a stir bar was flame dried, cooled under vacuum and purged with N2. To the flask were added 2-bromo-3-methylpyridine (5.2 ml, 29.1 mmol), N-bromosuccinimide (5.5 g, 32.0 mmol), and degassed benzene (126 ml). The flask was fitted with a condenser, heated to 40°C and AIBN (0.24 g, 1.5 mmol) was added in several portions. The reaction was irradiated using a sun lamp as it was stirred at 40°C.The reaction was monitored using TLC and HPLC and was stopped after 80percent conversion of the pyridine compound (approximately 8 hrs). The reaction was concentrated under reduced pressure, then redissolved in DCM/EtOAc (120 ml, 4:1 (v/v)) and extracted once with 50 ml of NaHCO3 (satd, aqueous) water and brine. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated. Upon standing the residue could not be fully redissolved in DCM and the resultant suspension was filtered to remove the insoluble solid. The filtrate was concentrated to near dryness and the residue was purified by normal phase flash chromatography (EtOAc/Hexanes) to give the title compound I-4 (3.0 g, 11.9 mmol, 41percent) as a yellow solid. H1 NMR (400 MHz, CDCl3) δ 8.33(1H, dd, J=5.2 Hz), 7.78(1H, dd, J=7.2 Hz), 7.28(1H, dd, J=5.4 Hz), 4.57(2H, s), MS (EC/MS) m/z observed 249.97, expected 249.89 [M+H].A mixture of 2-bromo-3-methylpyridine (2.0 mL, 17.9mmoli), NBS (3.5 g, 19.7 mmoli) and benzoyl peroxide (1.8 g, 10.2 mmoli) in CCl

Molecular Weight:250.92
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:250.87682
Monoisotopic Mass:248.87887
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes