Dichloromethane → HCID 71059520, compound

HRID 1425597Notes

Reaction equation

HRID 1425597 reaction equation
C(Cl)Cl.[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O)([O-:6])=[O:5].[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27](Br)=[N:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I.O>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N+:4]([O-:6])=[O:5])=[N:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 160946965-(Benzyloxy)-2-bromopyridine

Product 1

HCID 71059520HCID 71059520, compoundYield 51.7%

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 (0.077 g, 0.095 mmol) was added to a solution containing (2-nitrophenyl)boronic acid (0.316 g, 1.893 mmol), 5-(benzyloxy)-2-bromopyridine (0.5 g, 1.893 mmol), Copper(I) iodide (0.036 g, 0.189 mmol) and Potassium carbonate (1.420 ml, 2.84 mmol) in DMF (Volume: 6.31 ml). Let the reaction cool to room temperature. Diluted reaction with water, extracted with ethyl acetate, combined organics, dried, filtered and concentrated. Purified with Combiflash using 15% ethyl acetate in hexanes to afford 5-(benzyloxy)-2-(2-nitrophenyl)pyridine (0.3 g, 0.979 mmol, 51.7% yield).

Workup

  1. additionwas added to a solution
  2. additionDiluted
  3. extractionextracted with ethyl acetate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified with Combiflash

Sources & evidence

ORD record
ord-3b9d0094eddb47e3987cc3df363a9eda
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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