Reacción #8996

Ecuación de reacción

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

Tributyl-1-propynylstannane

sodium hydroxide

→

title compound

2-[[6-Methoxy-3-pyridinyl]methyl]amino-N-[4-(1-propynyl)-3-(trifluoromethyl)-phenyl]benzamide

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is then cooled
2. 2
   Otropurged with air for 2 hours
3. 3
   ExtracciónThe resulting mixture is extracted with ethyl acetate (3×100 mL)
4. 4
   LavadoThe organic phase is sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL)
5. 5
   Secadodried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Otrothe solvent is evaporated under reduced pressure
8. 8
   Otroto yield the crude product which
9. 9
   Otrois purified by column chromatography on silica gel, eluent 33% ethyl acetate in hexane
10. 10
    Otrorecrystallised from diethylether-hexane

Procedimiento

A stirred solution of 2-[[6-methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)-phenyl]benzamide (Reference Example 1; 3.98 g, 8.3 mmol) in dry toluene (200 mL) is purged with argon for 20 minutes at 25° C. Tributyl-1-propynylstannane (4.1 g of 80%, 9.96 mmol) and tetrakis(triphenylphosphine)palladium (0) (260 mg) are then added and the resulting mixture is heated at 100° C. for 17 hours under an argon atmosphere. The mixture is then cooled, treated with an aqueous solution of sodium hydroxide (85 mL of 0.1 M) and purged with air for 2 hours. The resulting mixture is extracted with ethyl acetate (3×100 mL). The organic phase is sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL), dried (Na2SO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 33% ethyl acetate in hexane and recrystallised from diethylether-hexane to give the title compound as a pale-yellow crystalline solid; m.p. 123–124° C.

Fuente