تفاعل #325449

معادلة التفاعل

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

2-cyanophenylboronic acid

cesium carbonate

→

title compound

المردود 51.6%

4-(2-Cyano-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

المردود 51.6%

المذيبات

water

—

IMS

DME

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe products were extracted into DCM
2. 2
   تجفيفdried over magnesium sulphate
3. 3
   ترشيحfiltered
4. 4
   أخرىthe solvent removed by evaporation under vacuum
5. 5
   أخرىThe residue was purified by flash chromatography on silica eluting with 0-20% ethyl acetate/hexane
6. 6
   workup.ADDITIONThe fractions containing the desired product
7. 7
   تركيزwere concentrated under vacuum

الإجراء التجريبي

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.5 g, 1.5 mmol), 2-cyanophenylboronic acid (0.23 g, 1.6 mmol), tetrakis-triphenylphosphine (0.17 g, 0.15 mmol) and cesium carbonate (0.73 g, 2.26 mmol) were dissolved in a mixture of DME (3 mL), IMS (1.0 mL) and water (0.4 mL) under argon. The mixture was heated by microwave irradiation to 120° C. for 0.3 hours then diluted with water. The products were extracted into DCM, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-20% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a yellow oil (0.22 g). LCMS m/z 261.2 [M+H]+. R.T.=4.59 min (Analytical Method 4).

المصدر