Cesium carbonate → HCID 86669967, compound

HRID 2273510Notes

Reaction equation

HRID 2273510 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:22]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:23]=2)[CH:5]=[C:6]([C:8]2[C:9]3[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[CH:21]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]=1.[C:40]1(B(O)O)[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:40]1([C:2]2[CH:3]=[C:4]([C:22]3[N:23]=[C:24]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:27]=3)[CH:5]=[C:6]([C:8]3[C:9]4[C:14]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=5[CH:21]=3)=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:7]=2)[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 86669966HCID 86669966, compound

Product 1

HCID 86669967HCID 86669967, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Then in a stream of argon, 0.5 g (0.96 mmol) of the obtained 2-[3-chloro-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine, 038 g (1.73 mmol) of 1-naphthaleneboronic acid, 12.9 mg (0.058 mmol) of palladium acetate and 1.13 g (3.46 mmol) of cesium carbonate were suspended in 50 mL of tetrahydrofuran, and the temperature of the obtained suspension was elevated to 70° C. and distilled under reflux for 40 hours. The resultant reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by column chromatography to give 0.56 g of the target 2-[3-(1-naphthyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine as grayish white solid (yield: 95%).

Workup

  1. customwas elevated to 70° C.
  2. distillationdistilled
  3. temperatureunder reflux for 40 hours
  4. customThe resultant reaction mixture
  5. distillationdistilled under a reduced pressure
  6. customto remove all volatile materials
  7. additionMethanol was added to the concentrate
  8. filtrationthe thus-deposited solid was collected by filtration
  9. customThe thus-obtained crude product
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ea7122c2f7b34ed3b4dd6a5bc2499961
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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