Sodium Hydroxide → 3-(Indolin-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

HRID 41121노트

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HRID 41121 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[S:16][C:17]([C:26]([F:29])([F:28])[F:27])=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=4)[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[S:16][C:17]([C:26]([F:27])([F:28])[F:29])=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=4)[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

참가 물질

5

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HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

생성물 1

HCID 251103473-(Indolin-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole수율 84.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
19 °C

실험 절차

To a stirred solution of 3-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole (40 mg, 0.097 mmol) in acetic acid at 12-14° C. was added slowly sodium cyanoborohydride (19 mg, 0.29 mmol). At the end of the addition the reaction was allowed to warm to 18-20° C. and was stirred for 2 h. After completion the reaction mixture was neutralized with 50% sodium hydroxide and extracted with ethyl acetate (50 ml×2). The organic layers were combined and dried over Na2SO4 and removed under reduced pressure. The crude indoline compound was purified by column chromatography using CH2Cl2/MeOH (9:1) to offer the product in 84.3% yield (33.8 mg, 0.082 mmol). MS (EI) m/z: 414 (M+)

후처리

  1. additionAt the end of the addition the reaction
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. dry with materialdried over Na2SO4
  4. customremoved under reduced pressure
  5. customThe crude indoline compound was purified by column chromatography

출처 및 근거

ORD 기록
ord-b4456bf4355445ca89dc62378c016e54
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530503B2

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