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 2244644ノート

反応式

HRID 2244644 の反応式
[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]

参加物

6

反応物 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

生成物 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)propanamide収率 20.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-401901ed9fad4e069814e66cfc7caeab
出典データセット
uspto-grants-2010_03
特許番号
US07678820B2

反応ノート

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