2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine → (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine

HRID 643008Notes

Reaction equation

HRID 643008 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=2)[CH:9]=1)=[N+]=[N-]>CCO.CC(O)=O.[Fe]>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]2[CH:9]=[C:5]([CH2:4][NH2:1])[N:6]=[CH:7]2)=[N:11][CH:12]=1

Participants

5

Reactant 1

HCID 866140062-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine

Product 1

HCID 68502878(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamineYield 55.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine (500 mg, 1.79 mmol) and iron powder (767 mg, 13.7 mmol) in EtOH (8 mL) and HOAc (6 mL) was heated at reflux for 2 h. It was filtered through celite. The filtrate was concentrated in vacuo. The residue was partitioned between 5% NaHCO3 and EtOAc. The biphasic solution was filtered. The EtOAc phase was separated, dried over Na2SO4, and concentrated in vacuo to give (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine (253 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationIt was filtered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between 5% NaHCO3 and EtOAc
  6. filtrationThe biphasic solution was filtered
  7. customThe EtOAc phase was separated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55b44155e890468e94800070c96ed5ae
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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