Diphenyl Ether → 7-Bromo-1,5-naphthyridin-4-ol

HRID 40370Notes

Reaction equation

HRID 40370 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]=[C:10]2[C:15](=[O:16])OC(C)(C)OC2=O)[CH:5]=[N:6][CH:7]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:15](=[O:16])[CH:10]=[CH:9][NH:8]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 675027485-((5-Bromopyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 134591367-Bromo-1,5-naphthyridin-4-olYield 84%

Conditions

Temperature
250 °C

Procedure

A 500 mL round bottom flask equipped with a reflux condenser was charged with 5-((5-bromopyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10.5 g, 32.1 mmol) and diphenyl ether (84.5 mL, 32.1 mmol). This was heated to 250° C. in heating mantle and allowed to stay at this temperature for 1 hour. Reaction mixture was cooled to room temperature and diluted with 300 mL of Hexanes. This was heated to 60° C. and triturated in this system for 3 hrs to afford 7-bromo-1,5-naphthyridin-4(1H)-one (6.05 g, 84% yield) as a crude brown solid. This was used without further purification. MS[M+H]=227.0. Calc'd for C8H5BrN2O=225.0.

Workup

  1. customA 500 mL round bottom flask equipped with a reflux condenser
  2. temperaturein heating mantle
  3. customReaction mixture
  4. temperaturewas cooled to room temperature
  5. temperatureThis was heated to 60° C.
  6. customtriturated in this system for 3 hrs

Sources & evidence

ORD record
ord-446bf2fdbbe04251977a1db310bcacb9
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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