Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1503371Generated: October 29, 2026

3-Cyanophenylboronic acid → 3-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile

https://huagongshe.com/reaction/1503371

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Cyanophenylboronic acidHCID 2734325—
Reactant6-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-oneHCID 58197583—
CatalystHCID 178418476HCID 178418476—
SolventCesium carbonateHCID 10796—
Solvent1,4-DioxaneHCID 31275—
Product3-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrileHCID 6658477620%

Reaction Steps

6-Bromo-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalen]-1(3H)-one (163 mg, 0.5 mmol), 3-cyanophenylboronic acid (147 g, 1 mmol) in [1,4]-dioxane (12 mL), Cs2CO3 (2 N, 3.2 mL), then Pd(PPh3)2Cl2 (5 mg, 0.01 mmol) was added under Ar2, the mixture was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by TLC to give 3-(1-oxo-1,3,3′,4′-tetrahydro-1′H-spiro[indene-2,2′-naphthalene]-6-yl)benzonitrile (35 mg, 6%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09212153B2
Source datasetuspto-grants-2015_12
ORD IDord-884a65917fdb45ad8ea6953c72bb3d60
Source noteuspto-grants-2015_12