Sodium Carbonate → HCID 59266212, compound

HRID 423236Notes

Reaction equation

HRID 423236 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][N:10]=[C:9]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[C:19]1([C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)=[CH:3][CH:4]=3)[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:11][N:10]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 59844934HCID 59844934, compound

Product 1

HCID 59266212HCID 59266212, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

Into a 100 mL three-neck flask were put 2.0 g (5.3 mmol) of 4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole, 0.98 g (8.0 mmol) of 3-pyridineboronic acid, and 0.28 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium(0), and 10 mL of 1,2-dimethoxyethane (DME) and 10 mL of a 2M sodium carbonate aqueous solution were added to the mixture. This mixture was degassed under reduced pressure. After that, the air in the flask was replaced with nitrogen. This mixture was stirred at 95° C. for 3 hours. After the stir, dichloromethane was added to the reacted mixture, and the suspension was washed with 1M diluted hydrochloric acid, a saturated sodium hydrogen carbonate solution, and saturated saline. The organic layer and the aqueous layer were separated. Magnesium sulfate was added to the organic layer to dry the organic layer. After the drying, this mixture was subjected to suction filtration through Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd.) to obtain the filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. For the column chromatography, first toluene and then a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=1:3) were used as developing solvents. The obtained fraction was concentrated to give a solid. The obtained solid was recrystallized with a mixed solvent of ethanol and hexane to give 1.5 g of a powdery white solid, which was the object of the synthesis, at a yield of 76%.

Workup

  1. customInto a 100 mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. additionAfter the stir, dichloromethane was added to the reacted mixture
  4. washthe suspension was washed with 1M diluted hydrochloric acid
  5. customThe organic layer and the aqueous layer were separated
  6. additionMagnesium sulfate was added to the organic layer
  7. customto dry the organic layer
  8. filtrationAfter the drying, this mixture was subjected to suction filtration through Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd.)
  9. customto obtain the filtrate
  10. concentrationThe obtained filtrate was concentrated
  11. custompurified by silica gel column chromatography
  12. concentrationThe obtained fraction was concentrated
  13. customto give a solid
  14. customThe obtained solid was recrystallized with a mixed solvent of ethanol and hexane

Sources & evidence

ORD record
ord-f629f3113ae044e79b38607586ee8a7f
Source dataset
uspto-grants-2012_01
Patent number
US08101771B2

Reaction notes

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