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

HRID 18216

Reaction equation

HRID 18216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:10](O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 9115786-Bromo-4H-imidazo[4,5-b]pyridine

Procedure

5-Bromo-2,3-diaminopyridine (1.69 g, 8.99 mmole) was taken up in 96% formic acid (50 mL) and heated to reflux. After 18 hr the mixture was cooled to RT and concentrated. The residue was taken up in H2O and the pH was adjusted to 7 with 2.0 M NaOH. The title compound (1.54 g, 87%) was collected as a solid by filtration, washed with H2O, and dried in vacuo: MS (ES) m/e 198/200 (M+H)+.

Workup

  1. temperatureheated to reflux
  2. concentrationconcentrated
  3. filtrationThe title compound (1.54 g, 87%) was collected as a solid by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-927531f2479049d7b1a9c998d4269d4f
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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