5-Bromo-3-nitropyridine-2-carbonitrile → 5-(3-Methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile

HRID 968624Notes

Reaction equation

HRID 968624 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br-].[CH3:14][C:15]1[C:16]([Zn+])=[N:17][CH:18]=[CH:19][CH:20]=1>C1COCC1.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>[CH3:14][C:15]1[C:16]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 178426320HCID 178426320, compound

Product 1

HCID 220302915-(3-Methyl(2-pyridyl))-3-nitropyridine-2-carbonitrileYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Heat a solution of 5-bromo-3-nitropyridine-2-carbonitrile (228 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg), 3-methyl-2-pyridylzinc bromide (0.5 M in THF, 3 mL, 1.5 mmol) in THF (5 mL) at 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (10 mL). Extract the aqueous layer with ethyl acetate (2×15 mL), wash with water (10 mL) and brine (10 mL), dry (MgSO4) and evaporate to give the title compound as a pale yellow solid (211 mg, 88%).

Workup

  1. temperatureCool the solution
  2. custompartition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (10 mL)
  3. extractionExtract the aqueous layer with ethyl acetate (2×15 mL)
  4. washwash with water (10 mL) and brine (10 mL)
  5. dry with materialdry (MgSO4)
  6. customevaporate

Sources & evidence

ORD record
ord-057796bed8e9400bae8d43320d8ce5af
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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