Sodium Hydroxide → 4-{5-[3-(Trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}indoline

HRID 552866노트

반응식

HRID 552866 반응식
[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[CH:23]=[CH: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].B(C#N)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CC(O)=O.O>[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][NH:25]4)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:12])([F:13])[F:14]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 592141764-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indoleHCID 86626745Sodium cyanoborate

생성물 1

HCID 592143624-{5-[3-(Trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}indoline수율 89.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole (100 mg) in AcOH (3 ml) was added portionwise sodium cyanoboroate (29 mg). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, alkalified with a 1M aqueous NaOH solution, and extracted with EtOAc. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10 to 75:25), and washed with n-hexane to obtain 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}indoline (90 mg) as a pale yellow solid.

후처리

  1. extractionextracted 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
  6. customthe residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10 to 75:25)
  7. washwashed with n-hexane

출처 및 근거

ORD 기록
ord-e012200ffcca4efab181b008c817553c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951825B2

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