Cesium carbonate → 3-(1-Oxo-1,1',3,3'-tetrahydrospiro[indene-2,2'-phenalene]-6-yl)benzonitrile

HRID 472990Notes

Reaction equation

Br[C:2]1[CH:22]=[C:21]2[C:5]([CH2:6][C:7]3([C:20]2=[O:23])[CH2:18][C:17]2[C:19]4[C:13]([CH:14]=[CH:15][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=4[CH2:8]3)=[CH:4][CH:3]=1.[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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:23]=[C:20]1[C:7]2([CH2:8][C:9]3[C:19]4[C:13]([CH:12]=[CH:11][CH:10]=3)=[CH:14][CH:15]=[CH:16][C:17]=4[CH2:18]2)[CH2:6][C:5]2[C:21]1=[CH:22][C:2]([C:30]1[CH:31]=[C:26]([CH:27]=[CH:28][CH:29]=1)[C:24]#[N:25])=[CH:3][CH:4]=2

Participants

Conditions

Temperature: 100 °C

Procedure

6-Bromo-1′,3′-dihydrospiro[indene-2,2′-phenalen]-1(3H)-one (200 mg, 0.57 mmol) and 3-cyanophenylboronic acid (168 mg, 1.17 mmol) was dissolved in 1,4-dioxane (5 mL), Cs2CO3 (0.6 mL, 2 M) was added. Then Pd(PPh3)2Cl2 (10 mg) was added under N2. The mixture was heated at 100° C. for 10 minutes under microwave. The solvent was removed in vacuum. The crude product was purified by preparative TLC to give 3-(1-oxo-1,1′,3,3′-tetrahydrospiro[indene-2,2′-phenalene]-6-yl)benzonitrile (130 mg, 60%).

Workup

customThe solvent was removed in vacuum
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-c8eb20b0b7c34b9189243d43d4c2cad5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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