Réaction #74420

Équation de réaction

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

Solvants

DMF

MeOH

Conditions de réaction

Traitement

1. 1
   Autrepurged twice with CO
2. 2
   TempératureAfter the reaction mixture was cooled to ambient temp.
3. 3
   Filtrationcontents were filtered through Celite
4. 4
   LavageThe Celite pad was washed with CH2Cl2
5. 5
   Séchagethe organic phase was dried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe crude material was purified

Mode opératoire

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).

Source