Reaktion #8992

Reaktionsgleichung

Sodium cyanoborohydride

6-methoxy-3-pyridinecarboxaldehyde

2-amino-N-(4-bromo-3-trifluoromethylphenyl)-benzamide

sodium hydrogen carbonate

→

title compound

2-[[6-Methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)phenyl]benzamide

Lösungsmittel

methanol

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is evaporated under reduced pressure
2. 2
   Sonstigeto give a residue which
3. 3
   Extraktionextracted with dichloromethane (3×150 mL)
4. 4
   TrocknenThe combined extracts are dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent is evaporated under reduced pressure
7. 7
   Sonstigeto yield the crude product that
8. 8
   Sonstigeis purified by column chromatography on silica gel, eluent 5% ethyl acetate in dichloromethane
9. 9
   Sonstigerecrystallised from diethylether-hexane

Vorschrift

Sodium cyanoborohydride (8.80 g of 95%, 133 mmol) is added in portions over 30 minutes to a stirred mixture of acetic acid (3.8 mL), 6-methoxy-3-pyridinecarboxaldehyde (Fluka, Buchs, Switzerland; 7.80 g, 57 mmol) and 2-amino-N-(4-bromo-3-trifluoromethylphenyl)-benzamide (step 1.2; 13.65 g, 38 mmol) in methanol (380 mL) at 25° C. The mixture is stirred for 16 hours. The solvent is evaporated under reduced pressure to give a residue which is treated with a saturated aqueous solution of sodium hydrogen carbonate (500 mL) and extracted with dichloromethane (3×150 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product that is purified by column chromatography on silica gel, eluent 5% ethyl acetate in dichloromethane and recrystallised from diethylether-hexane to give the title compound as a beige crystalline solid, m.p. 101–103° C.

Quelle