Sodium borohydride → [4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanol

HRID 1661938Notes

Reaction equation

HRID 1661938 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[N:9]([CH2:22][CH2:23][O:24][CH3:25])[C:8]=2[C:7]([O:26][CH3:27])=[CH:6][C:5]=1[CH:28]=[O:29]>C(O)C>[Br:3][C:4]1[C:12]2[N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:18]=3)[N:9]([CH2:22][CH2:23][O:24][CH3:25])[C:8]=2[C:7]([O:26][CH3:27])=[CH:6][C:5]=1[CH2:28][OH:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577720644-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

Product 1

HCID 57771990[4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanolYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (65 mg, 1.72 mmol) is added to a solution of 370 mg (0.858 mmol) 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde in 5 ml absolute ethanol at 0° C. The reaction mixture is stirred at 0° C. for 20 min. Then the reaction mixture is poured on water and extracted (3×) with dichloromethane/isopropanol (3:1). The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo to afford 380 mg of the title compound as a pure crystalline solid.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted (3×) with dichloromethane/isopropanol (3:1)
  3. washThe combined organic layers are washed with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fe16788774447129aa789493369ec2b
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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