6-Iodo-2,3-dimethoxypyridine → 5,6-Dimethoxypicolinonitrile

HRID 2368174Notes

Reaction equation

HRID 2368174 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5](I)[N:4]=1.[Cu](C#N)[C:13]#[N:14]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([C:13]#[N:14])[N:4]=1

Participants

4

Reactant 2

HCID 453617466-Iodo-2,3-dimethoxypyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 467367605,6-Dimethoxypicolinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,3-dimethoxy-6-iodopyridine (4-4, 24.0 g, 91 mmol) in DMF (181 mL) was added copper cyanide (9.73 g, 109 mmol) and heated to 150° C. for 20 minutes in a microwave reactor. The mixture was partitioned between saturated sodium carbonate and EtOAc three times. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 40% EtOAc in hexanes) to yield the desired product (4-5) as an off-white crystalline powder. ESI+MS [M+H]+ C8H8N2O2: 165.0 found, 165.1 required.

Workup

  1. customThe mixture was partitioned between saturated sodium carbonate and EtOAc three times
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by gradient elution on silica gel (0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3b29e7148ff4b978c421252d32eb7d8
Source dataset
uspto-grants-2014_04
Patent number
US08703770B2

Reaction notes

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