Water → HCID 89614873, compound

HRID 2203251Notes

Reaction equation

HRID 2203251 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.C([O-])([O-])=O.[K+].[K+].[CH3:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](F)=[CH:29][CH:28]=1)=[O:26].O>CS(C)=O>[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[N:8]3[C:30]1[CH:31]=[CH:32][C:27]([C:25](=[O:26])[CH3:24])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9196Benzo[a]carbazoleHCID 98284'-FluoroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 89614873HCID 89614873, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 11H-benzo[a]carbazole (2.00 g, 9.22 mmol) in DMSO (20 mL) is added K2CO3 (3.85 g, 27.9 mmol) at 180° C., and then the mixture is stirred for 1 hour. To the mixture is added 4-fluoroacetophenone (1.28 g, 9.228 mmol). After stirring for 8 hours, the reaction mixture is cooled to room temperature, and poured into water. The crude product is extracted with ethyl acetate, and it is washed with water and brine. The organic layer is dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain an off-white solid (160 mg; 5%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 2.75 (s), 7.20 (d), 7.23 (t), 7.34-7.46 (m), 7.65 (d), 7.75 (d), 8.00 (d), 8.19 (d), 8.22 (d), 8.25 (d).

Workup

  1. stirringAfter stirring for 8 hours
  2. extractionThe crude product is extracted with ethyl acetate, and it
  3. washis washed with water and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationAfter concentration
  6. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2
  7. customto obtain an off-white solid (160 mg; 5%)

Sources & evidence

ORD record
ord-7bafb5b9f2ad41f1af06cb25c1596b6e
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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