تفاعل #8992

معادلة التفاعل

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

المذيبات

methanol

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent is evaporated under reduced pressure
2. 2
   أخرىto give a residue which
3. 3
   استخلاصextracted with dichloromethane (3×150 mL)
4. 4
   تجفيفThe combined extracts are dried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent is evaporated under reduced pressure
7. 7
   أخرىto yield the crude product that
8. 8
   أخرىis purified by column chromatography on silica gel, eluent 5% ethyl acetate in dichloromethane
9. 9
   أخرىrecrystallised from diethylether-hexane

الإجراء التجريبي

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.

المصدر