Reaktion #1718069

Reaktionsgleichung

NaHCO3

5-bromo-3-pyridine-carboxaldehyde

methanesulfonamide

acetic acid

triethylamine

NaBH(OAc)3

→

N-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic phase is separated
2. 2
   ExtraktionThe aqueous phase is extracted with dichloromethane
3. 3
   Trocknenthe combined organic phase is dried over Na2SO4
4. 4
   EinengenConcentration
5. 5
   Sonstigeaffords a residue which
6. 6
   Sonstigeis purified by silica gel flash chromatography with a methanol in dichloromethane gradient

Vorschrift

To a solution of 5-bromo-3-pyridine-carboxaldehyde (1.5 g, 7.9 mmol), methanesulfonamide (0.5 g, 5.3 mmol), acetic acid (0.637 g, 10.6 mmol), triethylamine (1.07 g, 10.6 mmol) in DCE (50 mL) at ambient temperature is added NaBH(OAc)3 (3.14 g, 14.84 mmol). The reaction mixture is stirred overnight. Aqueous NaHCO3 (20 mL) is added and the organic phase is separated. The aqueous phase is extracted with dichloromethane and the combined organic phase is dried over Na2SO4. Concentration affords a residue which is purified by silica gel flash chromatography with a methanol in dichloromethane gradient to afford N-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide as a solid. MS (ESI) m/z 266.9 (M+H)+.

Quelle