Water → 2-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61717Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[C:11](=[CH:12][C:13]([C:20]#[N:21])=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:8]([CH3:23])([CH3:22])[C:7]=2[CH:24]=1.C1C(=O)N([Br:32])C(=O)C1.O>CC#N>[Br:32][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[C:20]#[N:21])[NH:10][C:9]1[C:8]([CH3:22])([CH3:23])[C:7]3[CH:24]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[C:18](=[O:19])[C:17]2=1

Participants

Conditions

Temperature: 80 °C

Procedure

8-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A5-2, 50 mg, 0.158 mmol) was dissolved in CH3CN (1 mL), added with NBS (56 mg, 2 eq.), and stirred at 80° C. overnight. The reaction solution was added to water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with MeOH and the solid remained after dissolution was filtered to obtain the target compound (yellow powder, 20 mg, 38%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
customThe drying agent was removed by filtration
customthe residues obtained
concentrationafter concentration under reduced pressure
additionwere added with MeOH
dissolutionafter dissolution
filtrationwas filtered
customto obtain the target compound (yellow powder, 20 mg, 38%)

Sources & evidence

ORD record: ord-d089bde9a01e42148730473b844ecee9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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