Dimethylformamide → 6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinonitrile

HRID 71180Notes

Reaction equation

HRID 71180 reaction equation
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:4][CH:3]=1.[CH3:16][N:17](C=O)C>C(OCC)(=O)C.N.[C-]#N.[Zn+2].[C-]#N.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>[CH3:9][O:8][C:6]1[N:7]=[C:2]([C:16]#[N:17])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

Product 1

HCID 666080866-Methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinonitrile

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 222AmmoniaSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Under a nitrogen atmosphere, to a mixture of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (25 g) and zinc cyanide (16.4 g) in DMF (250 mL) was added tetrakis(triphenylphosphine)palladium(0) (2.16 g) at room temperature, and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and 10% aqueous ammonia solution. The precipitate was collected by filtration, washed with ethyl acetate and dried to give the title compound (17.5 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-37eeb0021f474827b1f8f463763e6df1
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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