Sodium borohydride → (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanol

HRID 643006Notes

Reaction equation

HRID 643006 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9]2)=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866140051-(5-bromopyridin-2-yl)-1H-imidazole-4-carbaldehyde

Product 1

HCID 68511931(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanolYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-(5-bromopyridin-2-yl)-1H-imidazole-4-carbaldehyde (730 mg, 2.90 mmol) in MeOH (10 mL) at room temperature was added NaBH4 (134 mg, 3.53 mmol). The mixture was stirred for 30 min, during which time the suspension became clear. The solvent was removed in vacuo. The residue was partitioned between H2O and EtOAc. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanol as a solid (520 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between H2O and EtOAc
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e810aad404940188a7f1a0bc6802032
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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