Water → Trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:22])([CH3:21])[C:6]=2[CH:23]=1.[F:24][C:25]([F:31])([F:30])[S:26](O)(=[O:28])=[O:27].O>N1C=CC=CC=1>[C:19]([C:12]1[CH:11]=[C:10]2[C:15]([C:16]3[C:17](=[O:18])[C:5]4[CH:4]=[CH:3][C:2]([O:1][S:26]([C:25]([F:31])([F:30])[F:24])(=[O:28])=[O:27])=[CH:23][C:6]=4[C:7]([CH3:21])([CH3:22])[C:8]=3[NH:9]2)=[CH:14][CH:13]=1)#[N:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 550 mg, 0.189 mmol) was dissolved in pyridine (18 mL), added with anhydrous trifluoromethane sulfonic acid (0.758 ml, 3 eq.), and stirred at room temperature for 30 minutes. The reaction solution was poured into water and then extracted with dichloromethane. The organic layer was dried over magnesium 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 target compound (white powder, 641 mg, 81%).
Workup
- extractionextracted with dichloromethane
- dry with materialThe organic layer was dried over magnesium 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)
- customto obtain the target compound (white powder, 641 mg, 81%)
Sources & evidence
- ORD record
- ord-381d9b400ec04b34bae8a93d273789c0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365514B2
Reaction notes
Loading…