Potassium Carbonate → 5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine

HRID 1072792Notes

Reaction equation

HRID 1072792 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.[C:10](OCC)(OCC)(OCC)[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.ClCCl>[Br:9][C:4]1[N:3]=[C:2]2[N:1]=[C:10]([CH3:11])[NH:8][C:7]2=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66221Triethyl orthoacetateHCID 223883866-Bromopyridine-2,3-diamine

Product 1

HCID 223879615-bromo-2-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2,3-Diamino-6-bromopyridine (8.16 g) and triethyl orthoacetate (12.0 ml) were mixed in acetic acid (41 ml), and the mixture was refluxed under heating for 29 hr. The mixture was allowed to cool and the solvent was evaporated to give a crude product (10 g). This was dissolved in a sufficient amount of dichloromethane. Anhydrous potassium carbonate and active carbon were added and the mixture was stirred at room temperature. The insoluble matter was filtered off and the solvent was evaporated to give the objective compound (7.59 g) as a pale-yellow powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 29 hr
  3. temperatureto cool
  4. customthe solvent was evaporated
  5. customto give a crude product (10 g)
  6. filtrationThe insoluble matter was filtered off
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b2f35d86ae2147fc8b2dfb71baeddc57
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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