Water → 8-Methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61786

Reaction equation

Br[C:2]1[C:23]([O:24][CH3:25])=[CH:22][C:5]2[C:6]([CH3:21])([CH3:20])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11]([C:18]#[N:19])[CH:10]=4.[CH:26]([B-](F)(F)F)=[CH2:27].[K+].O>C(O)CC>[CH3:25][O:24][C:23]1[C:2]([CH:26]=[CH2:27])=[CH:3][C:4]2[C:16](=[O:17])[C:15]3[C:14]4[C:9](=[CH:10][C:11]([C:18]#[N:19])=[CH:12][CH:13]=4)[NH:8][C:7]=3[C:6]([CH3:20])([CH3:21])[C:5]=2[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E3-1-1, 50 mg, 0.13 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (1:1) (10.3 mg, 0.1 eq.), TEA (53 μl, 3 eq.) and potassium vinyltrifluoroborate (51 mg, 3 eq.) were dissolved in n-propanol and the mixture was stirred at 60° C. for 5 days. The reaction solution was added to water and then extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (brown powder, 25 mg, 19%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customThe drying agent was removed by filtration
customthe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-54492f4e782e40e88c592fe8d9e64e3b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Linked notes

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