Reacción #8992

Ecuación de reacción

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

Disolventes

methanol

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent is evaporated under reduced pressure
2. 2
   Otroto give a residue which
3. 3
   Extracciónextracted with dichloromethane (3×150 mL)
4. 4
   SecadoThe combined extracts are dried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent is evaporated under reduced pressure
7. 7
   Otroto yield the crude product that
8. 8
   Otrois purified by column chromatography on silica gel, eluent 5% ethyl acetate in dichloromethane
9. 9
   Otrorecrystallised from diethylether-hexane

Procedimiento

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.

Fuente