반응 #74420

반응 방정식

carbon monoxide

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

triphenylphosphine

potassium acetate

→

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

용매

DMF

MeOH

반응 조건

후처리

1. 1
   기타purged twice with CO
2. 2
   온도After the reaction mixture was cooled to ambient temp.
3. 3
   여과contents were filtered through Celite
4. 4
   세척The Celite pad was washed with CH2Cl2
5. 5
   건조the organic phase was dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude material was purified

실험 절차

A mixture of 5-(4-bromophenyl)-2-((S)-1-(4fluorophenyl)ethylamino)-5-methylthiazol-4(5H)-one (0.79 g, 1.9 mmol), triphenylphosphine (Aldrich, 0.15 g, 0.58 mmol), palladium acetate (Aldrich, 0.11 g, 0.48 mmol), potassium acetate (Aldrich, 0.24 g, 2.4 mmol), in MeOH (3 mL) and DMF (3 mL) was pressurized with carbon monoxide, purged twice with CO and then heated to 100° C. overnight at 40-50 psi of CO. After the reaction mixture was cooled to ambient temp., then contents were filtered through Celite. The Celite pad was washed with CH2Cl2, and the organic phase was dried over Na2SO4, concentrated in vacuo. The crude material was purified using silica gel chromatography. MS: 387 (M+1).

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