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Trifluoroacetic acid → HCID 86703316, 화합물

HRID 2409999
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인쇄 미리보기

반응식

HRID 2409999 반응식
[C:1](/[CH:3]=[CH:4]/[C:5]1[N:10]=[C:9]([CH2:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14](C(OC(C)(C)C)=O)[C:13]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:8]=[CH:7][CH:6]=1)#[N:2].FC(F)(F)C(O)=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C.ClCCl>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12]([CH2:11][C:9]3[N:10]=[C:5](/[CH:4]=[CH:3]/[C:1]#[N:2])[CH:6]=[CH:7][CH:8]=3)=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[NH:14]2)=[CH:19][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86703315HCID 86703315, 화합물

생성물 1

HCID 86703316HCID 86703316, 화합물수율 87.5%

시약·촉매·용매 1

HCID 21877088Acetonitrile methylene chloride
용매

실험 절차

To a solution of tert-butyl 3-[6-((E)-2-cyanovinyl)pyridin-2-ylmethyl]-6-methoxy-2-phenyl-1H-indole-1-carboxylate (100 mg) in acetonitrile/dichloromethane (1 mL/1 mL) was added trifluoroacetic acid (1 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (68.7 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.40 (2H, s), 6.60 (1H, d, J=16.1 Hz), 6.76 (1H, dd, J=2.1, 8.7 Hz), 6.91 (1H, d, J=2.1 Hz), 7.07-7.16 (2H, m), 7.32-7.49 (5H, m), 7.50-7.63 (3H, m), 8.05 (1H, br s).

후처리

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-0092d38833c5492d9a6dba00d6d75ed9
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815903B2

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