Cyclohexanone → 8-[4-(1-Cyano-cyclohexyl)-piperazin-1-yl]-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61870Notes

Reaction equation

[CH2:1]([C:3]1[C:24]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:23][C:6]2[C:7]([CH3:22])([CH3:21])[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[C:17](=[O:18])[C:5]=2[CH:4]=1)=[CH:14][CH:13]=[C:12]([C:19]#[N:20])[CH:11]=4)[CH3:2].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C[Si]([C:42]#[N:43])(C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.[I-].[Zn+2].[I-]>[C:42]([C:31]1([N:28]2[CH2:29][CH2:30][N:25]([C:24]3[C:3]([CH2:1][CH3:2])=[CH:4][C:5]4[C:17](=[O:18])[C:16]5[C:15]6[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=6)[NH:9][C:8]=5[C:7]([CH3:22])([CH3:21])[C:6]=4[CH:23]=3)[CH2:26][CH2:27]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)#[N:43]

Participants

Conditions

Temperature: 60 °C

Procedure

9-Ethyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (45 mg) and cyclohexanone (25 mg) were suspended in chloroform (2 ml), added with trimethylsilyl cyanide (30 mg) and zinc iodide (5 mg), and the mixture was stirred at 60° C. for 17 hrs. The reaction mixture was diluted with ethyl acetate (20 ml) and the organic layer was washed with 10% brine solution and concentrated under reduced pressure. The resulting residues were purified by silica gel column (dichloromethane/methanol (=99/1)) to obtain the title compound (12 mg, yield 30%).

Workup

washthe organic layer was washed with 10% brine solution
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by silica gel column (dichloromethane/methanol (=99/1))

Sources & evidence

ORD record: ord-f2f7d8e5a65e478fb48d3610106645e5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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