Reacción #74424

Ecuación de reacción

2-((S)-1-(2-fluorophenyl)ethylamino)-5-methylthiazol-4(5H)-one

4-bromobenzonitrile

2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene

NaN(TMS)2

→

4-(2-((S)-1-(2-fluorophenyl)ethylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)benzonitrile

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled to ambient temp.
2. 2
   Otroquenched with NH4Cl (5 mL)
3. 3
   ExtracciónThe reaction mixture was extract with EtOAc
4. 4
   SecadoThe organic phase was dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by silica gel chromatography

Procedimiento

To a mixture of 2-((S)-1-(2-fluorophenyl)ethylamino)-5-methylthiazol-4(5H)-one (0.0500 g, 0.198 mmol), 4-bromobenzonitrile (Aldrich, 0.0721 g, 0.396 mmol), Pd2(dba)3 (Aldrich, 0.0127 g, 0.0139 mmol), 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (Strem, 0.0123 g, 0.0198 mmol), and NaN(TMS)2 (Aldrich, 0.0727 g, 0.396 mmol) was added toluene (2 mL) in a dry box. The mixture was gradually heated to 95° C. and stirred overnight. The reaction was cooled to ambient temp. and quenched with NH4Cl (5 mL). The reaction mixture was extract with EtOAc. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. MS: 354 (M+1)

Fuente