3-Cyanophenylboronic acid → 3-(1'-Oxo-1',3',5,7,8,9-hexahydrospiro[benzo[7]annulene-6,2'-indene]-6'-yl)benzonitrile

HRID 472978Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6′-bromo-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2′-inden]-1′(3′H)-one (200 mg, 0.59 mmol) and 3-cyanophenylboronic acid (130 mg, 0.885 mmol) in Cs2CO3 (2 M, 1 mL) and 1,4-dioxane (4.2 mL) under N2 was added Pd(PPh3)2Cl2 (20 mg). The mixture was stirred at 100° C. for 0.7 h. After cooled to room temperature, the organic layer was dried and concentrated to give the residue, which was purified by TLC to give 3-(1′-oxo-1′,3′,5,7,8,9-hexahydrospiro[benzo[7]annulene-6,2′-indene]-6′-yl)benzonitrile (120 mg, 56%).

Workup

temperatureAfter cooled to room temperature
customthe organic layer was dried
concentrationconcentrated
customto give the residue, which
customwas purified by TLC

Sources & evidence

ORD record: ord-addfd8951e504c55a08701244d8fcbc2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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