Cesium carbonate → HCID 67984390, compound

HRID 2273488Notes

Reaction equation

HRID 2273488 reaction equation
Cl[N:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][CH:3]1[C:20]1[CH:21]=[C:22]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34](Cl)[CH:33]=2)[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1.[O:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH:41]=[C:40]1B(O)O.[C:51](=[O:54])([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)[C:64]2[CH:69]=[CH:68]C=C[C:65]=2[C:70]2C(C(C)C)=CC(C(C)C)=[CH:72][C:71]=2C(C)C)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH:41]=[C:40]1[C:34]1[CH:33]=[C:32]([C:22]2[CH:21]=[C:20]([C:3]3[N:4]=[C:5]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=[C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:2]=3)[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:68]4[O:54][C:51]5[CH:72]=[CH:71][CH:70]=[CH:65][C:64]=5[CH:69]=4)[CH:27]=3)[CH:23]=2)[CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86669948HCID 86669948, compound

Product 1

HCID 67984390HCID 67984390, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a stream of argon, 0.50 g (0.94 mmol) of 2-(3,3″-dichloro-(1,1′:3′,1″-terphenyl-5′-yl)-4,6-diphenylpyrimidine, 0.67 g (4.16 mmol) of benzofurylboronic acid, 1.35 g (4.16 mmol) of cesium carbonate, 8 mg (0.038 mmol) of palladium acetate and 36 mg (0.075 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were suspended in 20 mL of 1,4-dioxane, and the obtained suspension was heated under reflux for 14 hours. The reaction mixture was cooled to room temperature, and was 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 silica gel chromatography using a hexane/chloroform (1/1) mixed solvent as an eluent to give 0.16 g of the target 2-[3,3″-di(2-benzofuryl)-1,1′:3′,1″-terphenyl-5′-yl]-4,6-diphenylpyrimidine as a white solid (yield: 25%).

Workup

  1. temperaturethe obtained suspension was heated
  2. temperatureunder reflux for 14 hours
  3. distillationwas then distilled under a reduced pressure
  4. customto remove all volatile materials
  5. additionMethanol was added to the concentrate
  6. filtrationthe thus-deposited solid was collected by filtration
  7. customThe thus-obtained crude product
  8. customwas purified by silica gel chromatography
  9. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-d7171b736de545fa909e634e67862059
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

Loading…