반응 #46467

반응 방정식

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

반응 조건

후처리

1. 1
   workup.ADDITIONDimethylfomamide was added via syringe
2. 2
   기타the mixture evacuated
3. 3
   workup.ADDITIONrefilled with nitrogen
4. 4
   농축The mixture was concentrated under vacuum, water
5. 5
   workup.ADDITIONwas added
6. 6
   추출the mixture was extracted with ethyl acetate
7. 7
   건조The combined organic phase was dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure

실험 절차

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.

출처