Dimethylformamide → 5-Bromopyridine-2-carbonitrile

HRID 2100663Notes

Reaction equation

HRID 2100663 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][N:10](C=O)C>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.[O-]C#N.[Zn+2].[O-]C#N>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 693532,5-Dibromopyridine

Product 1

HCID 8171545-Bromopyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 178514111HCID 178514111, compoundCatalyst

Conditions

Temperature
135 °C

Procedure

2,5-Dibromopyridine (10 mmol), Pd(Ph3P)4 (0.3 mmol) and zinc cyanate (10 mmol) are mixed in DMF (12 mL) and purged with N2. The mixture is heated in a microwave reactor at 135° C. for 15 minutes, poured into saturated NH4Cl solution, and extracted with EtOAc. The combined extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (9:1 hexanes/EtOAc) to give 5-bromo-pyridine-2-carbonitrile.

Workup

  1. custompurged with N2
  2. additionpoured into saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe combined extracts are washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-d36829d94c8f46b289b84e3c282c961c
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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