HCID 77230174, compound → HCID 73554910, compound

HRID 595045Notes

Reaction equation

HRID 595045 reaction equation
[Cl:1][C:2]1[C:3](I)=[N:4][C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[Cu](C#N)[C:14]#[N:15]>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:14]#[N:15])=[N:4][C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 77230174HCID 77230174, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 73554910HCID 73554910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-chloro-2-iodo-5,6-dimethoxypyridine (1-6c, 230 mg, 0.768 mmol) in DMF (7.7 mL) was added copper cyanide (138 mg, 1.54 mmol) and heated to 150° C. for 20 minutes in a microwave reactor. The mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to yield the desired product (1-6d) as a bone-colored crystalline powder. ESI+ MS [M+H]+ C8H8ClN2O2=198.8.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a75f10ae74d4da48696a5c084e59246
Source dataset
uspto-grants-2016_01
Patent number
US09242995B2

Reaction notes

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