Water → HCID 59214248, compound

HRID 552848Notes

Reaction equation

HRID 552848 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4[CH2:22][C:23]([NH2:25])=[O:24])[N:9]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].[CH3:30][CH:31]([OH:33])[CH3:32].[H-].[Na+].O>CN(C=O)C>[CH:31]([O:33][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4[CH2:22][C:23]([NH2:25])=[O:24])[N:9]=2)=[CH:4][C:3]=1[C:26]([F:27])([F:29])[F:28])([CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 59214185HCID 59214185, compound

Product 1

HCID 59214248HCID 59214248, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)acetamide (100 mg) and 2-propanol (35 μl) in DMF (3 ml) was added 60% NaH (12 mg) at 0° C., followed by stirring at room temperature for 9 hours. The reaction solution was added with water (5 ml) to complete the reaction, and extracted with as a mixed solvent of chloroform:CH3OH (8:2). The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:CH3OH=98:2 to 93:7), and crystallized with diethyl ether to obtain 2-(4-{5-[4-isopropoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)acetamide (25 mg) as a pale yellow solid.

Workup

  1. customthe reaction
  2. extractionextracted with as a mixed solvent of chloroform:CH3OH (8:2)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=98:2 to 93:7)
  8. customcrystallized with diethyl ether

Sources & evidence

ORD record
ord-1f9b70f658be4c159da25ab3fdc2cd02
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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