Sodium Carbonate → HCID 59722056, compound

HRID 1513626Notes

Reaction equation

HRID 1513626 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[C:20]1([C:26]2[C:27]3[C:32]([C:33]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[C:34]4[C:39]=2[CH:38]=[C:37](B(O)O)[CH:36]=[CH:35]4)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:20]1([C:26]2[C:39]3[C:34]([C:33]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[C:32]4[C:27]=2[CH:28]=[C:29]([C:2]2[N:7]=[C:6]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[CH:5]=[C:4]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[N:3]=2)[CH:30]=[CH:31]4)=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 17125192-Bromo-4,6-diphenylpyrimidineHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Product 1

HCID 59722056HCID 59722056, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-4,6-diphenylpyrimidine 3.4 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 1,2-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 5.3 g (yield: 86%) of a greenish white solid matter. Mass spectral analysis of the above solid matter resulted in confirming that m/e was 560 versus a molecular weight of 560.23 and that it was the aimed compound 2.

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-f1e56baf94584951b0df073405a623d4
Source dataset
uspto-grants-2012_07
Patent number
US08217570B2

Reaction notes

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