تفاعل #74420

معادلة التفاعل

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

المذيبات

DMF

MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىpurged twice with CO
2. 2
   درجة الحرارةAfter the reaction mixture was cooled to ambient temp.
3. 3
   ترشيحcontents were filtered through Celite
4. 4
   غسيلThe Celite pad was washed with CH2Cl2
5. 5
   تجفيفthe organic phase was dried over Na2SO4
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude material was purified

الإجراء التجريبي

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).

المصدر