Dichloromethane → HCID 71059621, compound

HRID 1425595Notes

Reaction equation

HRID 1425595 reaction equation
C(Cl)Cl.Br[C:5]1[CH:6]=[C:7]([N+:17]([O-:19])=[O:18])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][CH:10]=1.[F:20][C:21]1[N:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I.O>[F:20][C:21]1[N:26]=[CH:25][C:24]([C:5]2[CH:10]=[N:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 71059550HCID 71059550, compound

Product 1

HCID 71059621HCID 71059621, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

[1,1′-Bis(diphenylphosphino)ferrocnee]dichloropalladium(II), w/DCM (7.32 mg, 8.96 μmol) was added to a solution containing 5-bromo-3-nitro-2-phenylpyridine (0.05 g, 0.179 mmol), (6-fluoropyridin-3-yl)boronic acid (0.025 g, 0.179 mmol), Copper(I) iodide (3.41 mg, 0.018 mmol) and Potassium carbonate (0.134 ml, 0.269 mmol) in DMF (Volume: 0.597 ml). Heated the reaction in a microwave at 110° C. for 15 minutes. Let the reaction cool to room temperature. Diluted reaction with water, dried, filtered, concentrated and purified with Combiflash using 0% to 25% ethyl acetate in hexanes to afford 6′-fluoro-5-nitro-6-phenyl-3,3′-bipyridine (0.03 g, 0.102 mmol, 56.7% yield).

Workup

  1. additionwas added to a solution
  2. temperatureHeated
  3. customthe reaction in a microwave at 110° C. for 15 minutes
  4. additionDiluted
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified with Combiflash

Sources & evidence

ORD record
ord-6aa0245c9988434c8f9be1f6e779fc17
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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