Sodium Methoxide → 8-Bromo-2,7-dimethoxy-1,5-naphthyridine

HRID 656875Notes

Reaction equation

HRID 656875 reaction equation
[Br:1][C:2]1[C:3](F)=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[CH3:15][O-:16].[Na+]>CO.O.[Cl-].[Na+].O>[Br:1][C:2]1[C:3]([O:16][CH3:15])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 454803208-Bromo-7-fluoro-2-methoxy-1,5-naphthyridine

Product 1

HCID 585793648-Bromo-2,7-dimethoxy-1,5-naphthyridineYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

8-Bromo-7-fluoro-2-(methoxy)-1,5-naphthyridine (for a synthesis see WO2004058144, example 53(g) (11.215 g, 43.64 mmol) was stirred in methanol (100 mL) at rt under argon and a solution of sodium methoxide in methanol (94 ml of a ca. 25% solution, 10 eq.) was added. The mixture was heated at 50° C. for 1 h. The mixture was allowed to cool to rt, then was diluted with water (500 ml) and brine (500 ml), and extracted with DCM (2×300 ml). The DCM extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give 8-bromo-2,7-bis(methoxy)-1,5-naphthyridine as a cream solid (11.21 g, 95%).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with DCM (2×300 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4188d68c8eb842049e18a118cabd3010
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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