반응 #74424

반응 방정식

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

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction was cooled to ambient temp.
2. 2
   기타quenched with NH4Cl (5 mL)
3. 3
   추출The reaction mixture was extract with EtOAc
4. 4
   건조The organic phase was dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude product was purified by silica gel chromatography

실험 절차

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)

출처