Formic Acid → 7-Bromo-1,6-naphthyridine-2-carboxylic acid

HRID 523076Notes

Reaction equation

HRID 523076 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](C)=[N:9]2)=[CH:4][N:3]=1.[Se](=O)=O.[CH:16]([OH:18])=[O:17].OO>O1CCOCC1.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 24007Selenium DioxideHCID 899956197-Bromo-2-methyl-1,6-naphthyridine

Product 1

HCID 899957427-Bromo-1,6-naphthyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

7-Bromo-2-methyl-1,6-napthyridine (Preparation 65, 206 mg, 0.92 mmol) and selenium dioxide (102.5 mg, 0.92 mmol) were heated in dioxane (3 mL) at 80° C. for 2 hours. The reaction was diluted with DCM (6 mL) and filtered through celite. The filter cake was washed with DCM (3×9 mL) and the combined filtrates concentrated in vacuo. The residue was stirred with formic acid (1 mL) and hydrogen peroxide (35% aqueous solution, 50 uL, 0.67 mmol) was added. The reaction was stirred at 0° C. for 1 hour before the reaction was quenched by the addition of palladium on charcoal (3 mg) and stirred for a further 20 minutes. The reaction was concentrated in vacuo to afford the title compound.

Workup

  1. filtrationfiltered through celite
  2. washThe filter cake was washed with DCM (3×9 mL)
  3. concentrationthe combined filtrates concentrated in vacuo
  4. additionwas added
  5. customwas quenched by the addition of palladium on charcoal (3 mg)
  6. stirringstirred for a further 20 minutes
  7. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-d6b41690d3d549a49de46b6223abac2e
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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