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

HRID 472955Notes

Reaction equation

HRID 472955 reaction equation
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C:7]3([C:17]2=[O:20])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]3)=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:20]=[C:17]1[C:7]2([CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH2:6][C:5]2[C:18]1=[CH:19][C:2]([C:27]1[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:21]#[N:22])=[CH:3][CH:4]=2

Participants

6

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 581975836-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-one

Product 1

HCID 665847763-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrileYield 20%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 10796Cesium carbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give the residue, which
  4. customwas purified by TLC

Sources & evidence

ORD record
ord-aded660add204825b923c83b2c42c1dd
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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