Ethyl Acetate → HCID 57958510, compound

HRID 1502567Notes

Reaction equation

HRID 1502567 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[Na+].[C:28](=[O:31])([O-])[O-].[Na+].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:42]([O:45][CH2:46][CH3:47])(=O)[CH3:43]>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.C1(C)C=CC=CC=1.O.C(O)C>[N:12]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:2]3[CH:3]=[CH:4][C:43]([C:42]4[O:45][C:46]5[CH:47]=[CH:26][CH:21]=[CH:22][C:23]=5[N:24]=4)=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:36]3[CH:37]=[CH:38][C:33]([C:13]4[O:31][C:28]5[CH:5]=[CH:8][CH:9]=[CH:10][C:11]=5[N:12]=4)=[CH:34][CH:35]=3)=[CH:3][CH:4]=2)[CH:9]=[CH:10][C:11]=1[C:21]1[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57958525HCID 57958525, compound

Product 1

HCID 57958510HCID 57958510, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Into a 100 mL three-neck flask, 0.83 g (1.8 mmol) of 5,6-bis(4-bromophenyl)-2,4′-bipyridine, 0.82 g (7.7 mmol) of carbonate sodium, 0.81 g (3.4 mmol) of phenylboronic acid, 20 mL of toluene, 4.0 mL of ethanol, and 10 mL of water were put. The mixture was degassed by being stirred under reduced pressure, and the atmosphere in the flask was substituted by nitrogen. 82 mg (0.071 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to this mixture, and stirred at 80 C.° for 12 hours under a nitrogen stream. After a certain time, the mixture was cooled to room temperature, and the precipitated solid was recovered by suction filtration. The obtained solid was dissolved in chloroform, and washed with water and a saturated saline, and the organic layer was dried over magnesium sulfate. The obtained mixture was subjected to gravity filtration, and the obtained filtrate was concentrated to give a solid. A toluene solution containing the obtained solid was dissolved in ethyl acetate, and the solution was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The filtrate was condensed to give a solid. The obtained solid was recrystallized with toluene/hexane, so that an objective substance, 0.69 g of white powder was obtained in a yield of 55%.

Workup

  1. customThe mixture was degassed
  2. stirringstirred at 80 C.° for 12 hours under a nitrogen stream
  3. filtrationthe precipitated solid was recovered by suction filtration
  4. dissolutionThe obtained solid was dissolved in chloroform
  5. washwashed with water
  6. dry with materiala saturated saline, and the organic layer was dried over magnesium sulfate
  7. filtrationThe obtained mixture was subjected to gravity filtration
  8. concentrationthe obtained filtrate was concentrated
  9. customto give a solid
  10. filtrationthe solution was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  11. customcondensed
  12. customto give a solid
  13. customThe obtained solid was recrystallized with toluene/hexane, so that an objective substance

Sources & evidence

ORD record
ord-fa0b43c1a17447b8bc6bb3b14cad1a0e
Source dataset
uspto-grants-2015_12
Patent number
US09209408B2

Reaction notes

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