HCID 22346311, compound → HCID 22346422, compound

HRID 897287Notes

Reaction equation

HRID 897287 reaction equation
[C:1]([O:9][C:10]1[C:11]([C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13](I)=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([Zn]C#N)#[N:26]>CN(C=O)C>[C:1]([O:9][C:10]1[C:11]([C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13]([C:25]#[N:26])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22346311HCID 22346311, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 22346422HCID 22346422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 8-(benzoyloxy)-5-iodo-1,6-naphthyridine-7-carboxylate (750 mg, 1.727 mmol) in anhydrous DMF (10 ml) was added dicyanozinc (142 mg, 1.21 mmol) and tetrakis(triphenylphospine)palladium(0) (299 mg, 0.26 mmol) and the solution was stirred at 85° C. overnight. The reaction was quenched with water and extracted with chloroform three times. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (17-55% EtOAc/Hexanes gradient elution) to provide a white solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with chloroform three times
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (17-55% EtOAc/Hexanes gradient elution)
  7. customto provide a white solid

Sources & evidence

ORD record
ord-44d0b5d7c4b84e34b675fc45c85d0d1f
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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