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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 564573Generated: October 29, 2026

Potassium Carbonate → 3'-[(8-Methyl-8-azabicyclo[3.2.1]oct-3-ylidene)methyl]-3-biphenylcarbonitrile

https://huagongshe.com/reaction/564573

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant3-Cyanophenylboronic acidHCID 2734325—
Reactant3-[(3-Bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octaneHCID 57813411—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product3'-[(8-Methyl-8-azabicyclo[3.2.1]oct-3-ylidene)methyl]-3-biphenylcarbonitrileHCID 6700567197%

Reaction Conditions

Temperature130 °C

Reaction Steps

To a solution of 3-[(3-bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane (1.17 g, 4 mmol) in p-dioxane (15 mL) and H2O (5 mL) was added (3-cyanophenyl) boronic acid (0.705 g, 4.80 mmol), Pd(PPh3) (0.185 g, 0.16 mmol), and K2CO3 (1.658 g, 12 mmol) and then the mixture was heated in a microwave oven at 130° C. for 20 min. The organic layer of the reaction mixture was separated, concentrated and purified by Combiflash chromatograph to afford 1.22 g (97%) of the title compound. LC-MS m/z 315 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067408B2
Source datasetuspto-grants-2011_11
ORD IDord-6851f137603c4d19a8815bb82ece5613
Source noteuspto-grants-2011_11