HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Cyanophenylboronic acid → 3-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Cyanophenylboronic acid | HCID 2734325 | — |
| Reactant | 6-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-one | HCID 58197583 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Cesium carbonate | HCID 10796 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile | HCID 66584776 | 20% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09212153B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-884a65917fdb45ad8ea6953c72bb3d60 |
| Source note | uspto-grants-2015_12 |