Water → (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanamine

HRID 559574Notes

Reaction equation

HRID 559574 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14]O)[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[I:8].[N-:16]=[N+]=[N-].[Na+].O.CCOC(C)=O>CC#N.O=S(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH2:16])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[I:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 66974146(1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol

Product 1

HCID 66974227(1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanamineYield 68.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a suspension of (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g, 1.23 mmol) in CH3CN (7 mL), SOCl2 (2.5 mL) was added. Upon the addition, the suspension became clear. It was then concentrated in vacuo. The residue was dissolved in DMF (7 mL), NaN3 (0.32 g, 4.92 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was dissolved in MeOH (6 mL), Ra—Ni (50% slurry in H2O, ˜200 mg) was added. The mixture was hydrogenated under balloon H2 for 2 h. It was then filtered through celite. The filtrate was concentrated in vacuo to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanamine as a solid (0.268 g).

Workup

  1. additionwas added
  2. additionUpon the addition
  3. concentrationIt was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in DMF (7 mL)
  5. customThe organic phase was separated
  6. washwashed with 5% NaHCO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in MeOH (6 mL)
  10. additionRa—Ni (50% slurry in H2O, ˜200 mg) was added
  11. waitThe mixture was hydrogenated under balloon H2 for 2 h
  12. filtrationIt was then filtered through celite
  13. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-61abd0b672844a729a9737df354dd523
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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