Ethanol → HCID 58993777, compound

HRID 1915032Notes

Reaction equation

HRID 1915032 reaction equation
[Br:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4](/[N:6]=[C:7]1/[N:8](C(=O)C2C=CC=CC=2Br)[CH:9]=[C:10]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:24]([F:27])([F:26])[F:25])[N:11]=[CH:12]/1)=[O:5].[Li+].[OH-].CCO.CCOC(C)=O>O>[Br:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[N:11][C:10]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:24]([F:25])([F:26])[F:27])=[CH:9][N:8]=1)=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 178487288HCID 178487288, compound

Product 1

HCID 58993777HCID 58993777, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 50 mL round bottom flask was placed (E)-2-bromo-N-[1-(2-bromo-benzoyl)-5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-1H-pyrazin-2-ylidene]-benzamide (vi) (50 mg, 0.07 mmol). To this was added LiOH (100 mg), followed by EtOH (25 mL). The resulting solution was allowed to react, with stirring, for 30 minutes while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE=1:2). After completion, the resulting solution was diluted with 15 mL of H2O and extracted two times with 10 mL of EtOAc. The organic layers were combined and dried over Na2SO4. After removal of the solvent and volatile components under vacuum, the residue was purified by eluting through a silica gel column with a 1:6 EtOAc/PE solvent system. This resulted in 10 mg (27%) of the final product 2-bromo-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-yl]-benzamide (Compound 85) as a white solid.

Workup

  1. customInto a 50 mL round bottom flask was placed
  2. customto react
  3. extractionextracted two times with 10 mL of EtOAc
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent and volatile components under vacuum
  6. customthe residue was purified
  7. washby eluting through a silica gel column with a 1:6 EtOAc/PE solvent system

Sources & evidence

ORD record
ord-9e2531d5fe74403393f6cdebaf7edaa1
Source dataset
uspto-grants-2013_12
Patent number
US08614321B2

Reaction notes

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