1,4-Dioxane → HCID 57702763, compound

HRID 221181Notes

Reaction equation

HRID 221181 reaction equation
CC1(C)C(C)(C)OB(C2C=[CH:11][C:12]3[N:13]([C:31]4[C:40]5[C:35](=CC=CC=5)[CH:34]=CC=4)[C:14]4[C:19]([C:20]=3C=2)=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=4)O1.Br[C:43]1[CH:44]=[CH:45][C:46]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[N:47][CH:48]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:68][CH2:67]OCC1>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>[N:47]1[CH:48]=[C:43]([C:17]2[CH:16]=[CH:15][C:14]3[N:13]([C:31]4[C:67]5[C:68](=[CH:11][CH:12]=[CH:20][CH:19]=5)[CH:34]=[CH:35][CH:40]=4)[C:12]4[C:20]([C:19]=3[CH:18]=2)=[CH:16][C:15]([C:43]2[CH:44]=[CH:45][C:46]([C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)=[N:47][CH:48]=2)=[CH:14][CH:11]=4)[CH:44]=[CH:45][C:46]=1[C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 113906775-Bromo-2,3'-bipyridineHCID 67248907HCID 67248907, compound

Product 1

HCID 57702763HCID 57702763, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Into a flask, 1.50 g of 3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-9-naphthalene-1-yl-carbazole, 1.32 g of 5-bromo-2,3′-bipyridine, 194 mg of Pd(PPh3)4, 2.40 g of tripotassium phosphate, 25 ml of 1,4-dioxane, and 5 ml of water were put, and the solution was stirred at reflux temperature for 10 hours under argon atmosphere. After heating, the reaction liquid was cooled to room temperature, and washed by a saturated sodium chloride aqueous solution. The organic layer was concentrated in an evaporator, and the concentrates were washed by methanol. After washing, the concentrates were purified by silica gel column chromatography, recrystallized in a chloroform/ethyl acetate mixed solvent, and thus 475 mg of 3,6-bis(2,3′-bipyridine-5-yl)-9-naphthalene-1-yl-carbazole was obtained.

Workup

  1. temperatureat reflux temperature for 10 hours under argon atmosphere
  2. temperatureAfter heating
  3. customthe reaction liquid
  4. washwashed by a saturated sodium chloride aqueous solution
  5. concentrationThe organic layer was concentrated in an evaporator
  6. washthe concentrates were washed by methanol
  7. washAfter washing
  8. customthe concentrates were purified by silica gel column chromatography
  9. customrecrystallized in a chloroform/ethyl acetate mixed solvent

Sources & evidence

ORD record
ord-75895d19050741e2ac92c983464826b3
Source dataset
uspto-grants-2012_06
Patent number
US08202633B2

Reaction notes

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