Urea → 6-bromo-3H-imidazo[4,5-b]pyridin-2-ol

HRID 2036808Notes

Reaction equation

HRID 2036808 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.N[C:11](N)=[O:12]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[NH:9][C:11](=[O:12])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 1176UreaHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 19244136-bromo-3H-imidazo[4,5-b]pyridin-2-olYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromopyridine-2,3-diamine (2 g, 10.6 mmol) and urea (2.5 g, 41.6 mmol) was dissolved in DMF and heated to 100° C. for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over Na2SO4 then concentrated to provide 6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.80 g, 36%) as an off white solid which was used without further purification. LCMS Method W: retention time 0.98 min; [M+2]=212, 214.0.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationthen concentrated

Sources & evidence

ORD record
ord-564ea6b7a14342cdb402caa0ced2076e
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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