Reacción #7178

Ecuación de reacción

ethyl acetate

Intermediate 4

4-[2-(tert-butoxycarbonylamino)ethoxy]-N-(3-iodophenyl)-3-methoxyphenylacetamide

3-methylvinylbenzene

tris(2-methylphenyl)phosphine

→

4-[2-(tert-butoxycarbonylamino)-ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide

Rendimiento 152.4%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture is heated
2. 2
   Lavadothe mixture is washed with water and 2 M hydrochloric acid
3. 3
   SecadoThe organic layer is dried over sodium sulfate
4. 4
   Otrothe solvent is evaporated under reduced pressure
5. 5
   OtroThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Procedimiento

Intermediate 4 (1 g) is dissolved in dimethylformamide (10 ml), and thereto are added 3-methylvinylbenzene (826 mg), palladium (II) acetate (105 mg), tris(2-methylphenyl)phosphine (143 mg), tetra-n-butyl ammonium chloride (130 mg), and the mixture is heated with stirring at 97° C. for 18 hours under argon atmosphere. To the reaction solution is added ethyl acetate, and the mixture is washed with water and 2 M hydrochloric acid. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-[2-(tert-butoxycarbonylamino)-ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (370 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (120 mg).

Fuente