Water → HCID 89628071, compound

HRID 2203248Notes

Reaction equation

HRID 2203248 reaction equation
[CH2:1]([O:3][C:4](=[O:43])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[C:17]1[C:12]2=[CH:13][C:14]([C:34](=[O:42])[C:35]2[CH:40]=[CH:39][C:38](F)=[CH:37][CH:36]=2)=[C:15]2[CH:33]=[CH:32][CH:31]=[CH:30][C:16]2=1)=[O:8])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH:50]1[C:62]2[NH:61][C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:54]=2[CH:53]=[CH:52][CH:51]=1.O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:43])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[C:17]1[C:12]2=[CH:13][C:14]([C:34](=[O:42])[C:35]2[CH:40]=[CH:39][C:38]([N:61]3[C:62]4[CH:50]=[CH:51][CH:52]=[CH:53][C:54]=4[C:55]4[C:60]3=[CH:59][CH:58]=[CH:57][CH:56]=4)=[CH:37][CH:36]=2)=[C:15]2[CH:33]=[CH:32][CH:31]=[CH:30][C:16]2=1)=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 89627670HCID 89627670, compound

Product 1

HCID 89628071HCID 89628071, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To 4-(11-(2-ethylhexyl)-5-(4-fluoro-benzoyl)-11H-benzo[a]carbazol-8-yl]-4-oxo-butyric acid ethyl ester (1.01 g, 1.75 mmol) in dimethylsulfoxide (DMSO) (10 mL) are added K2CO3 (738 mg, 5.33 mmol) and carbazole (297 mg, 1.77 mmol). The reaction mixture is heated to 150° C. and stirred overnight. After cooling to room temperature, the reaction mixture is poured into water, and the crude product is extracted with CH2Cl2. The organic layer is washed with water and brine, dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain a brown resin (760 mg; 60%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.84 (t), 0.92 (t), 1.20-1.52 (m), 2.28-2.36 (m), 2.82 (t), 3.48 (t), 4.16 (q), 4.74-4.21 (m), 7.33 (t), 7.46 (t), 7.60 (d), 7.63 (d), 7.68 (t), 7.72 (t), 7.77 (d), 8.15 (t), 8.19 (d), 8.22 (d), 8.50 (s), 8.58 (d), 8.67 (d), 8.81 (s).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe crude product is extracted with CH2Cl2
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration
  6. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2
  7. customto obtain a brown resin (760 mg; 60%)

Sources & evidence

ORD record
ord-3bea2791fae14f96b3be13ac69fe1139
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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