Formamidine acetate → 5-bromo-3-(2-chloro-pyridin-4-yl)-3-H-imidazo[4,5-b]pyridine

HRID 1524197Notes

Reaction equation

HRID 1524197 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1.[C:17](O)(=O)C.C(N)=N>CCO.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=3)[CH:17]=[N:16][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 1317331266-Bromo-N*2*-(2-chloro-pyridin-4-yl)-pyridine-2,3-diamine

Product 1

HCID 866518705-bromo-3-(2-chloro-pyridin-4-yl)-3-H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6-Bromo-N*2*-(2-chloro-pyridin-4-yl)-pyridine-2,3-diamine (step 2)(1 eq, 1.22 mmol, 634 mg) is dissolved in EtOH (15 mL) and treated formamidine acetate (5 eq, 6.105 mmol, 634 mg). The reaction is heated at reflux for 3 hours allowed to cool to room temperature. The mixture is diluted with saturated aqueous sodium bicarbonate and extracted with EtOAc (3×10 ml). The organic portions are combined, dried (MgSO4) and concentrated in vacuo. Purification of the residue by flash chromatography on silica eluting at 5-10% EtOAc in hexane affords the title compound; [M+H]+=310.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with EtOAc (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica eluting at 5-10% EtOAc in hexane

Sources & evidence

ORD record
ord-74df8ecf6af143d6b2de460cce8d6a0d
Source dataset
uspto-grants-2015_07
Patent number
US09079897B2

Reaction notes

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