Potassium Carbonate → 3-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2,3-dihydro-1H-indol-1-yl)propanamide

HRID 552854Notes

Reaction equation

HRID 552854 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[CH2:23][CH2:24][NH:25]4)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:14])([F:13])[F:12].C([O-])([O-])=O.[K+].[K+].I[CH2:39][CH2:40][C:41]([NH2:43])=[O:42].C([O-])(O)=O.[Na+]>C(#N)C>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[CH2:23][CH2:24][N:25]4[CH2:39][CH2:40][C:41]([NH2:43])=[O:42])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5417403-IodopropanamideHCID 592143624-{5-[3-(Trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}indoline

Product 1

HCID 592142583-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2,3-dihydro-1H-indol-1-yl)propanamideYield 20.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy]phenyl]-1,2,4-oxadiazol-3-yl)indoline (100 mg) in acetonitrile (2.5 ml) was added K2CO3 (46 mg) and 3-iodopropanamide (124 mg) at room temperature, followed by stirring at 80° C. for 15 hours. To the reaction solution was added an NaHCO3 aqueous saturated solution, followed by extraction with EtOAc. 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=100:0 to 90:10) to obtain 3-(4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2,3-dihydro-1H-indol-1-yl)propanamide (23.6 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=100:0 to 90:10)

Sources & evidence

ORD record
ord-f1bec6d3e4ca4e82b602e633c2753d9b
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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