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With triethylamine In dichloromethane at -15℃; for 2h;
AM.C Step C:
MsCl (1.42 mL, 18.4 mmol) was added dropwise to a -15 °C solution of (3-bromo-5-chloropyridin-2-yl)methanol (3.72 g, 16.7 mmol) and triethylamine (4.66 mL, 33.4 mmol) in DCM (50 mL). The resulting mixture was allowed to stir at same temperature for 2 hours. The reaction mixture was quenched with water and diluted with EtOAc, and the aqueous layer was separated. The organic layer was washed with brine, dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to get crude. The crude was purified by silica gel column chromatography (15-20% EtO Ac/hexane) to get (3-bromo-5- chloropyridin-2-yl)methyl methanesulfonate (3.8 g, 76% yield) as a semisolid m/z (esi) M+l = 302.0.
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With methanol; sodium tetrahydroborate at 0 - 20℃; for 16.5h;
AM.B Step B:
Sodium borohydride (4.37 g, 1 15.7 mmol) was added in small portions to a cooled (0 °C) solution of methyl 3-bromo-5-chloropicolinate (4.8 g, 19.3 mmol) in methanol (70 mL) over approximately 30 minutes. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine, and MeOH was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S0 , filtered, and evaporated to get (3-bromo-5- chloropyridin-2-yl)methanol (3.72 g, 88% yield) as a semisolid m/z (esi) M+1 = 224.0.
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