Sodium Carbonate → 8,8-Dimethyl-3-(9-phenyl-9H-carbazol-3-yl)-8H-10,12b-diaza-benzo[a]aceanthrylene

HRID 1472511Notes

Reaction equation

HRID 1472511 reaction equation
[CH3:1][C:2]1([CH3:25])[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[N:10]2[C:17]3[C:7]([C:8]4[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18][C:9]=42)=[CH:6][CH:5]=[CH:4][C:3]1=3.Br[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:32]3[C:37]([C:38]=2[CH:39]=1)=[CH:36][CH:35]=[CH:34][CH:33]=3.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH3:1][C:2]1([CH3:25])[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[N:10]2[C:17]3[C:7]([C:8]4[CH:21]=[C:20]([C:35]5[CH:34]=[CH:33][C:32]6[N:31]([C:40]7[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=7)[C:30]7[C:38]([C:37]=6[CH:36]=5)=[CH:39][CH:27]=[CH:28][CH:29]=7)[CH:19]=[CH:18][C:9]=42)=[CH:6][CH:5]=[CH:4][C:3]1=3

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 189426243-Bromo-9-phenylcarbazoleHCID 672019818,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

Product 1

HCID 706652888,8-Dimethyl-3-(9-phenyl-9H-carbazol-3-yl)-8H-10,12b-diaza-benzo[a]aceanthrylene

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

36 g (110 mmol) of 8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid, 35 g (110 mmol) of 3-bromo-9-phenyl-9H-carbazole and 9.7 g (92 mmol) of sodium carbonate are suspended in 350 ml of toluene, 350 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water each time and subsequently evaporated to dryness. The residue is recrystallised from toluene and from CH2Cl2/isopropanol and finally sublimed in a high vacuum. Yield: 50 g (99 mmol), 89% of theory, purity according to HPLC 99.9%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water each time
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from CH2Cl2/isopropanol

Sources & evidence

ORD record
ord-4a97019daae64505adfb0fb65671feea
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

Loading…