Isopropanol → HCID 67163609, compound

HRID 2244641Notes

Reaction equation

HRID 2244641 reaction equation
[H-].[Na+].[CH3:3][CH:4](O)[CH3:5].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][N:24]4[CH2:29][C:30]([NH2:32])=[O:31])[N:16]=2)[CH:11]=[CH:12][C:13]=1F.[NH4+].[Cl-]>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][N:24]4[CH2:29][C:30]([NH2:32])=[O:31])[N:16]=2)[CH:11]=[CH:12][C:13]=1[CH:4]([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59214221HCID 59214221, compound

Product 1

HCID 67163609HCID 67163609, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60% NaH (43 mg) in DMF (4 ml) was added 2-propanol (65 mg) at 0° C., followed by stirring at room temperature for 20 min. After cooling to 0° C. again, 2-{4-[5-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl-acetamide (200 mg) was added thereto. The reaction mixture was radiated with a microwave at 60° C. for 50 min. The reaction solution was added to an aqueous NH4Cl solution, followed by stirring, and then the solvent was evaporated. After adding a mixed solvent (4:1) of chloroform-CH3OH, and suspending, the solid was removed, silica gel was added thereto, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=100:0 to 98:2; n-hexane:EtOAc=0:100) to obtain 2-{4-[5-(3-chloro-4-isopropylphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl}acetamide (17.5 mg) as a white solid.

Workup

  1. temperatureAfter cooling to 0° C. again
  2. waitThe reaction mixture was radiated with a microwave at 60° C. for 50 min
  3. stirringby stirring
  4. customthe solvent was evaporated
  5. additionAfter adding a mixed solvent (4:1) of chloroform-CH3OH
  6. customthe solid was removed
  7. additionsilica gel was added
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=100:0 to 98:2; n-hexane:EtOAc=0:100)

Sources & evidence

ORD record
ord-44a67cf1c0194f1e910dad44986a1e56
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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