Water → HCID 59214248, compound

HRID 2244638Notes

Reaction equation

HRID 2244638 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-7fbce6e19a91416687c4b61a5789ac68
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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