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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 472974Generated: October 25, 2026

3-Cyanophenylboronic acid → 3-(4-Methoxy-1'-oxo-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-6'-yl)benzonitrile

https://huagongshe.com/reaction/472974

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Cyanophenylboronic acidHCID 2734325—
Reactant6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-oneHCID 58197263—
CatalystHCID 178418476HCID 178418476—
SolventCesium carbonateHCID 10796—
Solvent1,4-DioxaneHCID 31275—
Product3-(4-Methoxy-1'-oxo-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-6'-yl)benzonitrileHCID 6704416446.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of 6′-bromo-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (40 mg, 0.130 mmol) and 3-cyanophenylboronic acid (30.5 mg, 0.208 mmol) in Cs2CO3 (2 M, 0.247 mL) and 1,4-dioxane (1.2 mL) under N2 was added Pd(PPh3)2Cl2 (7.5 mg). The mixture was stirred at 100° C. for 6 minutes. After cooled to room temperature, the organic layer was dried and concentrated to give the residue, which was purified by TLC to give 3-(4-methoxy-1′-oxo-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-6′-yl)benzonitrile (20 mg, 46%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633212B2
Source datasetuspto-grants-2014_01
ORD IDord-6e35da0fbb1048de942df736b721b9fb
Source noteuspto-grants-2014_01