Toluene → HCID 67540920, compound

HRID 579679Notes

Reaction equation

HRID 579679 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][CH:9]([CH3:33])[CH2:10][N:11]1[C:23]2[CH:22]=[CH:21][C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.Br[C:35]1[CH:36]=[CH:37][C:38]2[NH:39][C:40]3[C:45]([C:46]=2[CH:47]=1)=[CH:44][C:43](Br)=[CH:42][CH:41]=3.C([O-])([O-])=O.[Na+].[Na+]>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.O>[CH3:8][CH:9]([CH3:33])[CH2:10][N:11]1[C:12]2[CH:13]=[CH:14][C:15]([C:35]3[CH:36]=[CH:37][C:38]4[NH:39][C:40]5[C:45]([C:46]=4[CH:47]=3)=[CH:44][C:43]([C:20]3[CH:21]=[CH:22][C:23]4[N:11]([CH2:10][CH:9]([CH3:33])[CH3:8])[C:12]6[C:17]([C:18]=4[CH:19]=3)=[CH:16][CH:15]=[CH:14][CH:13]=6)=[CH:42][CH:41]=5)=[CH:16][C:7]=2[C:1]2[C:6]1=[CH:5][CH:4]=[CH:3][CH:2]=2

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2748743,6-DibromocarbazoleHCID 57668735HCID 57668735, compound

Product 1

HCID 67540920HCID 67540920, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Toluene (10 ml) and H2O (1 ml) were added into a mixture of 4 (0.25 g, 0.72 mmol), 3,6-dibromocarbazole (0.12 g, 0.36 mmol), Pd(PPh3)4 (0.04 g, 0.036 mmol) and Na2CO3 (0.37 g, 3.6 mmol). The reaction mixture was stirred at 90° C. for 12 hours, cooled to room temperature, and then extracted with methylene chloride. The organic extracts were combined, washed with water, and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 2:1 (v/v) as the eluent to yield 7 (0.27 g, 61%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ (ppm) 8.49-8.44 (d, 4H), 8.21-8.19 (d, 2H), 8.10 (s, broad, 1H), 7.86-7.81 (m, 4H), 7.57-7.42 (m, 8H), 7.27-7.24 (m, 2H), 7.30-7.23 (m, 2H), 4.15-4.10 (m, 4H), 2.45-2.38 (m, 2H), 1.03-0.99 (m, 12H), 4.16-4.14 (d, 4H), 2.46-2.43 (m, 2H), 1.04-1.02 (d, 12H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customUpon evaporating off the solvent
  6. customthe crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 2:1 (v/v) as the eluent

Sources & evidence

ORD record
ord-ad504f318398480a8523a8f7ad30aaf6
Source dataset
uspto-grants-2015_05
Patent number
US09040718B2

Reaction notes

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