2H-Pyran-4-carbonitrile, tetrahydro-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- synthesis
- Product Name:2H-Pyran-4-carbonitrile, tetrahydro-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-
- CAS Number:1206640-91-6
- Molecular formula:C18H24BNO3
- Molecular Weight:313.2
Yield:1206640-91-6 81%
Reaction Conditions:
with potassium acetate;tricyclohexylphosphine;bis(dibenzylideneacetone)-palladium(0) in 1,4-dioxane at 150; for 0.25 h;Microwave irradiation;
Steps:
6.22
A solution of 4-(4-chlorophenyl)tetrahydro-2H-pyran-4-carbonitrile (889 mg, 4.0 mmol), Pd(dba)2 (138 mg, 0.24 mmol), PCy3 (268 mg, 0.96 mmol), diboron pinacol ester (1.21 g, 4.8 mmol) and KOAc (1.18 g, 12.0 mmol) in 16 mL dioxane was microwave heated to 150° C. for 15 min. The resulting mixture was filtered, then concentrated and purified by flash chromatography on silica (2-5% MeOH/DCM eluent) to provide 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile as a yellow crystalline solid (1.01 g, 81% yield).
References:
US2012/225857,2012,A1 Location in patent:Page/Page column 17
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