Ethanol → HCID 118253616, compound

HRID 716603Notes

Reaction equation

HRID 716603 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[C:10](=[CH:11][CH:12]=[C:13]4[C:21]=3[NH:20][C:19]3[C:14]4=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[C:4]=2[CH:3]=1.[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH3:44][CH2:45]O>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.C1(C)C=CC=CC=1>[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[C:10](=[CH:11][CH:12]=[C:13]4[C:21]=3[NH:20][C:19]3[C:14]4=[CH:15][C:16]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[C:44]4[CH:45]=[CH:13][CH:21]=[CH:9][CH:10]=4)=[CH:17][CH:18]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 4589187Biphenyl-2-boronic acidHCID 12136728HCID 12136728, compound

Product 1

HCID 118253616HCID 118253616, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 15.3 g (37 mmol) of 3,8-dibromo-11,12-dihydroindolo[2,3-a]carbazole, 18.3 g (92.4 mmol) of biphenyl-2-ylboronic acid, 0.86 g (0.8 mmol) of Pd(PPh3)4, 55 ml of 2M Na2CO3, 100 ml of EtOH and 200 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica to give product (12.2 g, 21.8 mmol, 59%).

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe organic layer was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-fafcda1c627b494b95667ad6e1a56fd4
Source dataset
uspto-grants-2015_11
Patent number
US09190619B2

Reaction notes

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