Réaction #46467

Équation de réaction

3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

potassium carbonate

→

4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONDimethylfomamide was added via syringe
2. 2
   Autrethe mixture evacuated
3. 3
   workup.ADDITIONrefilled with nitrogen
4. 4
   ConcentrationThe mixture was concentrated under vacuum, water
5. 5
   workup.ADDITIONwas added
6. 6
   Extractionthe mixture was extracted with ethyl acetate
7. 7
   SéchageThe combined organic phase was dried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a flask was added 3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile (0.13 gm, 0.40 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.161 gm, 0.52 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium (0.020 gm, 0.0245 mmol), and potassium carbonate (0.124 gm, 0.9 mmol). Dimethylfomamide was added via syringe and the mixture evacuated and refilled with nitrogen, then heated for 16 hours at 80° C. The mixture was concentrated under vacuum, water was added, and the mixture was extracted with ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give crude 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a residue that was used directly in the next step without further characterization.

Source