1,4-Dioxane → HCID 57702785, compound

HRID 221177Notes

Reaction equation

HRID 221177 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]3[C:15]([C:16](B4OC(C)(C)C(C)(C)O4)=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)O1.Br[C:34]1[CH:35]=[CH:36][C:37]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[N:38][CH:39]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:59][CH2:58]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:38]1[CH:39]=[C:34]([C:16]2[C:17]3[C:18]([C:9]([C:34]4[CH:35]=[CH:36][C:37]([C:40]5[CH:41]=[N:42][CH:43]=[CH:58][CH:59]=5)=[N:38][CH:39]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:35]=[CH:36][C:37]=1[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 113906775-Bromo-2,3'-bipyridineHCID 574156912,2'-(Anthracene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Product 1

HCID 57702785HCID 57702785, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

Into a flask, 2.53 g of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)anthracene, 2 g of 5-bromo-2,3′-bipyridine, 960 mg of Pd(PPh3)4, 3.81 g of tripotassium phosphate, 60 ml of dioxane, and 15 ml of pure water were put, and the solution was stirred at reflux temperature for 3 days under argon atmosphere. After heating, the reaction liquid was cooled to room temperature, pure water was added, and then the organic layer was extracted. The organic layer was concentrated in an evaporator, the concentrates were purified by column chromatography, yellow powders which were concentrated again and obtained were washed by toluene, and thus 800 mg of 9,10-bis(2,3′-bipyridine-5-yl)anthracene was obtained. 1H-NMR (CDCl3) δ 7.4-7.6 (m, 6H), 7.2-7.3 (m, 4H), 8.0 (d, 4H), 8.5 (s, 2H), 8.8 (d, 4H), 9.4 (s, 2H).

Workup

  1. temperatureat reflux temperature for 3 days under argon atmosphere
  2. temperatureAfter heating
  3. customthe reaction liquid
  4. extractionthe organic layer was extracted
  5. concentrationThe organic layer was concentrated in an evaporator
  6. customthe concentrates were purified by column chromatography, yellow powders which
  7. concentrationwere concentrated again
  8. customobtained
  9. washwere washed by toluene

Sources & evidence

ORD record
ord-a514af0b10ab49229831f11549f19ea4
Source dataset
uspto-grants-2012_06
Patent number
US08202633B2

Reaction notes

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