Formic Acid → 6-Bromo-4H-imidazo[4,5-b]pyridine

HRID 1506222Notes

Reaction equation

HRID 1506222 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH:10](O)=O>>[Br:9][C:5]1[CH:6]=[C:7]2[N:8]=[CH:10][NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Procedure

2,3-Diamino-5-bromopyridine (4.10 g, 21.8 mmol) in formic acid (25 mL) was stirred at 100° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure, and the resulting residue was mixed with water and adjusted to pH 8 or above with saturated aqueous sodium hydrogen carbonate. The precipitated solid was collected by filtration, washed with water and chloroform and dried under reduced pressure to give the title compound as a dark brown solid (4.13 g, yield 96%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe resulting residue was mixed with water
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and chloroform
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7fe1f8ffecf14747854f74b16f5897a9
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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