Potassium Carbonate → 1,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Cyanophenylboronic acid	HCID 2734325	—
Reactant	Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate	HCID 57813409	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate	HCID 67005869	85.4%

Reaction Conditions

Temperature	130 °C

Reaction Steps

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate (2.07 g, 5.88 mmol) in p-dioxane (30 mL) and H2O (10 mL) was added (3-cyanophenyl)boronic acid (1.036 g, 7.05 mmol), Pd(PPh3) (0.272 g, 0.235 mmol), and K2CO3 (2.436 g, 17.63 mmol) and then the reaction was heated in a microwave at 130° C. for 15 minutes. The organic layer of the reaction mixture was separated, concentrated and purified by Combiflash chromatograph to afford 1.88 g (85%) of the title compound. LC-MS m/z 749 (2M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08067408B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-a05dac54005349b08cf1ad8f9d50ee1c
Source note	uspto-grants-2011_11