Dimethylformamide → HCID 68778454, compound

HRID 1711181Notes

Reaction equation

HRID 1711181 reaction equation
Br[C:2]1[C:3]([CH3:12])=[CH:4][C:5]2[N:6]([CH:9]=[CH:10][N:11]=2)[C:7]=1[CH3:8].[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].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]>[CH3:8][C:7]1[N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=[C:3]([CH3:12])[C:2]=1[C:13]#[N:14]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 68775112HCID 68775112, compound

Product 1

HCID 68778454HCID 68778454, compoundYield 99%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

6-Bromo-5,7-dimethyl-imidazo[1,2-a]pyridine (985 mg, 4.26 mmol) was dissolved in DMF (15 ml). To this solution was added Zn(CN)2 (512 mg, 4.36 mmol), Pd2(dba)3 (40 mg, 0.044 mmol) and DPPF (49 mg, 0.088 mmol). The mixture was heated at 120° C. for 48 h. The mixture was then concentrated under vacuum and the residue was taken into CH2Cl2 (40 ml) and washed with H2O (30 ml×2) and brine (20 ml). The organic layer was concentrated and the residue was purified by column chromatography on silica gel (CH2Cl2/CH3OH, 18:1) to give 5,7-dimethyl-imidazo[1,2-a]pyridine-6-carbonitrile (747 mg, 99%).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. washwashed with H2O (30 ml×2) and brine (20 ml)
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by column chromatography on silica gel (CH2Cl2/CH3OH, 18:1)

Sources & evidence

ORD record
ord-1585c0683b7647089d79c63f9cb6311f
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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