3,5-Dibromopyridine → HCID 18187614, compound

HRID 1624431Notes

Reaction equation

HRID 1624431 reaction equation
[CH2:1]([Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15](Br)[CH:16]=1>C1COCC1.[Cl-].[Zn+2].[Cl-].[Cu]I.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([C:15]1[CH:14]=[N:13][CH:12]=[C:11]([Br:10])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 693693,5-DibromopyridineHCID 178419663HCID 178419663, compound

Product 1

HCID 18187614HCID 18187614, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3007855ZincchlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Benzylmagnesium bromide (1.0 M in THF, 20 mL, 20 mmol) was added to a solution of zinc chloride (2.73 g, 20 mmol) in THF (20 mL) and the reaction was heated to 50° C. for 2.5 hours. The solution was then added by cannula to a solution of 3,5-dibromo-pyridine (3.07 g, 13 mmol), copper(I) iodide (0.0148 g, 0.78 mmol), and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.048 g, 0.65 mmol) in THF (20 mL). The reaction was heated to 50° C. for 48 hours then quenched with H2O, submitted to standard aqueous workup, and purified via silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. temperatureThe reaction was heated to 50° C. for 48 hours
  2. customthen quenched with H2O
  3. custompurified via silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-38b105fd3cb343f4b857adc0ea1cd853
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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