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

HRID 1920979Notes

Reaction equation

HRID 1920979 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-7c75849cb6df431ca96aaf6658e48784
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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