Reaktion #1710689

Reaktionsgleichung

5-bromo-3-pyridinecarboxaldehyde

ethanesulfonamide

acetic acid

triethylamine

sodium triacetoxyborohydride

→

ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide

Lösungsmittel

dichloromethane

sodium bicarbonate

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted two additional times with dichloromethane
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%)

Vorschrift

To a solution of 5-bromo-3-pyridinecarboxaldehyde (CAS#113118-81-3, 450 mg, 2.4 mmol) in dichloroethane (15 mL) was added ethanesulfonamide (CAS#1520-70-3, 175 mg, 1.6 mmol), acetic acid (0.18 mL 3.2 mmol), triethylamine (0.45 mL, 3.2 mmol) and sodium triacetoxyborohydride (1.0 g, 4.8 mmol). The reaction was stirred at room temperature for 3 hours, at which time it was diluted with dichloromethane and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide; MS: (ES+) m/z 278.9 (M+H)+.

Quelle