2-Bromo-6-phenylpyridine → HCID 59722065, compound

HRID 1513623Notes

Reaction equation

HRID 1513623 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.[C:14]1([C:20]2[C:21]3[C:26]([C:27]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[C:28]4[C:33]=2[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29]4)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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.C(=O)([O-])[O-].[Na+].[Na+]>[C:14]1([C:20]2[C:33]3[C:28]([C:27]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[C:26]4[C:21]=2[CH:22]=[C:23]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[N:3]=2)[CH:24]=[CH:25]4)=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 5686792-Bromo-6-phenylpyridineHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Product 1

HCID 59722065HCID 59722065, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

2-Bromo-6-phenylpyridine 2.5 g (11 mmol), 9,10-diphenylanthracene-2-boronic acid 4.9 g (13 mmol) and tetrakis(triphenylphosphine)palladium 0.25 g (0.22 mmol) were dissolved in 60 mL of 12-dimethoxyethane. A 2.0M sodium carbonate aqueous solution 30 mL was added thereto, and the solution was refluxed for 8 hours under argon atmosphere by heating. After finishing the reaction, the solution was filtered, and a solid matter obtained was washed with water, methanol and toluene to obtain 4.5 g (yield: 84%) of a greenish white solid matter. Mass spectral analysis of the above solid matter resulted in confirming that the measured value m/e was 483 versus a molecular weight of 483.20 and that it was the aimed compound 1

Workup

  1. temperaturethe solution was refluxed for 8 hours under argon atmosphere
  2. temperatureby heating
  3. customthe reaction
  4. filtrationthe solution was filtered
  5. customa solid matter obtained
  6. washwas washed with water, methanol and toluene

Sources & evidence

ORD record
ord-46f77c9a68354df59114d363acc0c034
Source dataset
uspto-grants-2012_07
Patent number
US08217570B2

Reaction notes

Loading…