Sodium borohydride → HCID 57772051, compound

HRID 1661950Notes

Reaction equation

HRID 1661950 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:29][CH3:30])=[CH:20][C:21]([CH:27]=[O:28])=[C:22]([C:23]([F:26])([F:25])[F:24])[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:29][CH3:30])=[CH:20][C:21]([CH2:27][OH:28])=[C:22]([C:23]([F:24])([F:25])[F:26])[C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57772019HCID 57772019, compound

Product 1

HCID 57772051HCID 57772051, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 710 mg (1.69 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-trifluoromethyl-1H-benzoimidazole-5-carbaldehyde (example 54c) in 5 ml ethanol, 128 mg (3.38 mmol) NaBH4 are added at 0° C. The mixture is stirred for 30 min at room temperature. Then the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is crystallized from hexane/EtOAc to afford 655 mg of the title compound as a colorless crystalline solid.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted (3×) with ethyl acetate
  3. washThe combined organic layers are washed with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallized from hexane/EtOAc

Sources & evidence

ORD record
ord-0d7b1fbc0bd24181b490884e06c75804
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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