Sodium Carbonate → 2-(2,4-Dichlorophenyl)-6-chloro-3-nitropyridine

HRID 1823521Notes

Reaction equation

HRID 1823521 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 2734659(2,4-Dichlorophenyl)boronic acid

Product 1

HCID 221429302-(2,4-Dichlorophenyl)-6-chloro-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

1 mmol 2,6-dichloro-3-nitropyridine, 1.05 mmol of 2,4-dichlorobenzeneboronic acid, and 3 mmol of Na2CO3, were dissolved in 1.5 ml THF and 0.5 ml water and purged with nitrogen. 0.05 mmol of [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) was added to reaction and stirred at room temperature under nitrogen for fourteen hours. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, and purified by column chromatography eluting with 10% ethylacetate 90% hexanes to obtain 2-(2,4-dichlorophenyl)-6-chloro-3-nitropyridine.

Workup

  1. custom0.5 ml water and purged with nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water and ethyl acetate
  4. extractionThe solution was extracted three times with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. custompurified by column chromatography
  7. washeluting with 10% ethylacetate 90% hexanes

Sources & evidence

ORD record
ord-6993b674706247bdad26dde6f38892fd
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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