Aluminium lithium hydride → HCID 58542017, compound

HRID 1966789Notes

Reaction equation

HRID 1966789 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[C:6]([C:15]2[N:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]3[CH:24]=[CH:25][C:26]([Br:28])=[CH:27][C:17]=3[N:16]=2)[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:28][C:26]1[CH:25]=[CH:24][C:18]2[N:19]([C:20]([CH3:21])([CH3:23])[CH3:22])[C:15]([C:6]3[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=3[N:10]3[CH:14]=[N:13][CH:12]=[N:11]3)=[N:16][C:17]=2[CH:27]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58542003HCID 58542003, compound

Product 1

HCID 58542017HCID 58542017, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-bromo-1-tert-butyl-1H-benzoimidazol-2-yl)-4-[1,2,4]triazol-1-yl-benzoic acid methyl ester (100 mg, 0.22 mmol) in dry THF (2 mL) is added Lithium aluminium hydride (LiAlH) (17 mg, 0.45 mmol). The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with saturated NaHCO3 (10 mL), extracted with EtOAc (3×10 mL). The organic layer is separated, washed with brine (10 mL), dried under anhydrous Na2SO4 (500 mg), and is filtered and concentrated. The residue is purified by silica gel flash chromatography with 0-5% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford [3-(5-bromo-1-tert-butyl-1H-benzoimidazol-2-yl)-4-[1,2,4]triazol-1-yl-phenyl]-methanol (47 mg, 50%).

Workup

  1. customThe reaction mixture is quenched with saturated NaHCO3 (10 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. customThe organic layer is separated
  4. washwashed with brine (10 mL)
  5. customdried under anhydrous Na2SO4 (500 mg)
  6. filtrationis filtered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel flash chromatography with 0-5% MeOH/CH2Cl2 as the eluent
  9. customThe product fractions are collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bf15741e9daa4afe934b9f838545a8fa
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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