2-Methyl-2-butene → HCID 178466118, compound

HRID 552863Notes

Reaction equation

HRID 552863 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[C:19]([CH:22]=4)[CH:20]=[O:21])[O:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.P([O-])(O)(O)=[O:31].[K+].CC(=CC)C.[Cl:41]([O-])=O.[Na+]>CC(O)(C)C.O>[ClH:41].[NH:3]1[C:4]2[CH:9]=[CH:8][C:7]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:29])[C:25]([F:27])([F:28])[F:26])=[C:19]([CH:22]=4)[C:20]([OH:31])=[O:21])[O:12][N:11]=3)=[CH:6][C:5]=2[N:1]=[CH:2]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 59214390HCID 59214390, compound

Product 1

HCID 178466118HCID 178466118, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixed solution of 5-[3-(1H-benzimidazol-6-yl)-1,2,4-oxadiazol-5-yl]-2-(2,2,2-trifluoro-1-methylethoxy)benzaldehyde (83 mg), potassium dihydrogen phosphate (421 mg), and 2-methyl-2-butene (0.5 ml) in tBuOH (2 ml) and water (0.5 ml) was added sodium chlorite (187 mg) at room temperature. The mixed reaction solution was stirred at room temperature for 3 hours, followed by dilution with water (10 ml), and extraction with EtOAc (20 ml). The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. To a solution of the residue in dioxane was added a 4 N HCl-dioxane solution, followed by concentration. The resulting powder was recrystallized with IPA (10 ml) to obtain 5-[3-(1H-benzimidazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid hydrochloride (80 mg) as white powders.

Workup

  1. customThe mixed reaction solution
  2. extractionfollowed by dilution with water (10 ml), and extraction with EtOAc (20 ml)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. additionTo a solution of the residue in dioxane was added a 4 N HCl-dioxane solution
  8. concentrationfollowed by concentration
  9. customThe resulting powder was recrystallized with IPA (10 ml)

Sources & evidence

ORD record
ord-809350cd7aed4e56bbe8dd2103a41861
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

Loading…