Toluene → HCID 86696083, compound

HRID 2172409Notes

Reaction equation

HRID 2172409 reaction equation
[C:1]1([N:7]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[C:8]2[C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:42]1([CH3:48])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:46]1[C:47]2[NH:7][C:1]3[C:48](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:42]=2[CH:43]=[C:44]([C:24]2[CH:23]=[CH:22][C:21]([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]4[S:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=5[C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:26][CH:25]=2)[CH:45]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 86696084HCID 86696084, compound

Product 1

HCID 86696083HCID 86696083, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]thiophen-4-amine (5.9 g, 12.4 mmol), 3-bromocabazole (3.5 g, 14.2 mmol), K2CO3 (16.6 g, 120.0 mmol) in toluene (150 mL), water (50 mL) and EtOH (50 mL) was bubbled for 30 min. Pd(PPh3)4 (0.4 g, 0.4 mmol) was added. The mixture was bubbled for 15 min. The resultant mixture was refluxed for 12 h. After cooling, the reaction mixture was extracted by CH2Cl2 and dried by MgSO4. The solvent was removed in vacuo and the residue was purified by flash chromatography using 25-50% CH2Cl2/hexane to afford N-(4-(9H-carbazol-3-yl)phenyl)-N-phenyldibenzo[b,d]thiophen-4-amine (5.8 g, 91% yield) as a white solid.

Workup

  1. customThe mixture was bubbled for 15 min
  2. temperatureThe resultant mixture was refluxed for 12 h
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted by CH2Cl2
  5. dry with materialdried by MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-142fdbf6253d42319689ade404c64a1b
Source dataset
uspto-grants-2015_06
Patent number
US09054323B2

Reaction notes

Loading…