Water → 6-(1H-Imidazol-2-yl)picolinonitrile

HRID 916665Notes

Reaction equation

HRID 916665 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[N:3]=1.O.[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2]>[NH:12]1[CH:11]=[CH:10][N:9]=[C:8]1[C:4]1[N:3]=[C:2]([C:14]#[N:15])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 575033132-chloro-6-(1H-imidazol-2-yl)pyridine

Product 1

HCID 232080316-(1H-Imidazol-2-yl)picolinonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
40 °C

Procedure

A mixture of 2-chloro-6-(1H-imidazol-2-yl)-pyridine (800 mg, 4.45 mmol), zinc cyanide (313 mg, 2.68 mmol), Pd2(dba)3 (122 mg, 0.133 mmol), DPPF (144 mg, 0.27 mmol) and water (0.1 mL) in DMF (10 mL) is degassed with argon for 15 minutes. The mixture is then heated at 40° C. overnight in a sealed tube. Solvent is removed and water (30 mL) is added and the mixture is extracted with methylene chloride. On drying (MgSO4), the solvent is removed. Column separation gives the product (172).

Workup

  1. customis degassed with argon for 15 minutes
  2. customSolvent is removed
  3. additionwater (30 mL) is added
  4. extractionthe mixture is extracted with methylene chloride
  5. dry with materialOn drying (MgSO4)
  6. customthe solvent is removed
  7. customColumn separation

Sources & evidence

ORD record
ord-fd84e3eaea18487aa78ef074fc16521a
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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