Diisopropylethylamine → 2-Propyl-4-(trifluoromethyl)-1-{[5-(3,4,5-trifluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-1H-indole-5-carbonitrile

HRID 913665노트

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HRID 913665 반응식
[C:1]([C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13](=[NH:16])[NH:14][OH:15])[C:7]([CH2:17][CH2:18][CH3:19])=[CH:6]2)#[N:2].[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([F:35])[C:33]=1[F:34])[C:28](Cl)=O.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:17]([C:7]1[N:8]([CH2:12][C:13]2[N:16]=[C:28]([C:27]3[CH:26]=[C:25]([F:24])[C:33]([F:34])=[C:32]([F:35])[CH:31]=3)[O:15][N:14]=2)[C:9]2[C:5]([CH:6]=1)=[C:4]([C:20]([F:22])([F:23])[F:21])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH2:18][CH3:19]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27770233,4,5-Trifluorobenzoyl chlorideHCID 178438386HCID 178438386, 화합물

생성물 1

HCID 578003842-Propyl-4-(trifluoromethyl)-1-{[5-(3,4,5-trifluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-1H-indole-5-carbonitrile수율 45.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
150 °C

실험 절차

To a solution of 2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol) in anhydrous acetonitrile (3.0 mL) under N2, was added 3,4,5-trifluorobenzoyl chloride (0.241 g, 1.23 mmol) and N,N-diisopropylethylamine (0.50 mL, 5.21 mmol). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.065 g (45% yield) of pure product: MS (ES) m/z 464 (M+).

후처리

  1. temperatureUpon cooling
  2. additionthe mixture was poured onto a biotage prepak column
  3. customthe mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient)

출처 및 근거

ORD 기록
ord-be5b9c398fc047a5bf2764d3c11a42e9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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