تفاعل #47442

معادلة التفاعل

tributyl(vinyl)tin

(S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester

(S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide

ethyl acetate

→

(S)-2-[4-(2-fluoro-3-vinyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester

المردود 73.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىdilute hydrochloric acid and separated
2. 2
   غسيلThe organic phase was washed with, saturated sodium bicarbonate solution
3. 3
   تجفيفa saturated sodium chloride solution and dried over sodium sulfate
4. 4
   ترشيحThe mixture was filtered
5. 5
   أخرىevaporated
6. 6
   أخرىthe residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 10% to 50% ethyl acetate/hexanes) which

الإجراء التجريبي

To a mixture of (S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (prepared as in Example 128, 0.624 g, 1.51 mmol), tetrakis(triphenylphosphine)palladium(0) (0.200 g, 0.17 mmol) in N,N-dimethylformamide (7 mL) was added tributyl(vinyl)tin (0.652 g, 2.05 mmol) and the resulting mixture stirred at 80° C. for 14 h. The mixture was taken up in ethyl acetate and dilute hydrochloric acid and separated. The organic phase was washed with, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over sodium sulfate. The mixture was filtered, evaporated and the residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 50 g, 10% to 50% ethyl acetate/hexanes) which afforded (S)-2-[4-(2-fluoro-3-vinyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (0.400 g, 73%) as a clear oil.

المصدر