Ethyl orthoformate → HCID 178419455, compound

HRID 2409026Notes

Reaction equation

HRID 2409026 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[CH:10](OCC)(OCC)OCC>>[Br:1][C:2]1[C:3]2[NH:9][CH:10]=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 78369Pyridine, 3-bromo-4,5-diamino-

Product 1

HCID 178419455HCID 178419455, compoundYield 75%

Procedure

To a solution of 5-bromopyridine-3,4-diamine (12 g, 63 mmol) in (EtO)3CH (150 mL) was added camphorsulfuric acid (0.5 g). The reaction mixture was heated at reflux for 2 h then the EtOH was distilled to afford a solid. The solid was filtered to afford 9.5 g (75%) 7-bromo-1H-imidazo[4,5-c]pyridine as a white solid; MS (ESI) m/z: 199.0 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. distillationthe EtOH was distilled
  4. customto afford a solid
  5. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-2cd76289d742496f9d7424d2b7a2bb2b
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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