Sodium Carbonate → HCID 67110563, compound

HRID 1627750Notes

Reaction equation

HRID 1627750 reaction equation
[C:1]1([C:7]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]3[C:15]4=[C:16](C5C=CC=CC=5[N:14]4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=4)[CH:17]=[C:18](B(O)O)[CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:37]1[N:42]=[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:40]=[C:39]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[N:38]=1.C(=O)([O-])[O-].[Na+].[Na+].O1[CH2:66][CH2:65]OCC1>C1(C)C=CC=CC=1.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>[C:66]1([C:37]2[N:42]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:40]=[C:39]([C:49]3[CH:54]=[C:53]4[C:52]5=[C:51]([C:8]6[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=6[N:14]5[C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=5[C:7]4([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:50]=3)[N:38]=2)[CH:65]=[CH:3][CH:2]=[CH:1][CH:6]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 312751,4-DioxaneHCID 67109979HCID 67109979, compound

Product 1

HCID 67110563HCID 67110563, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

20 g (44 mmol) of 8,8-diphenyl-8H-indolo[3,2,1-de]acridine-6-boronic acid, 11.7 g (44 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 2.9 g (27.4 mmol) of sodium carbonate are suspended in 70 ml of toluene, 70 ml of dioxane and 50 ml of water. 1.44 mg (1.24 mmol) of Pd(PPh3)4 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 and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 22.4 g (35 mmol), corresponding to 80% of theory.

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
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-4a1f01767f7148cc8f0067b8d4ef2abe
Source dataset
uspto-grants-2014_07
Patent number
US08785636B2

Reaction notes

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