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Potassium Iodide → Tert-butyl [4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl](3-phenylpropyl)carbamate

HRID 452763
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HRID 452763 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)=[N:17][N:18]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:31]1([CH2:37][CH2:38][CH2:39]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[N:7]([C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)=[N:17][N:18]=2)[CH:11]=[CH:10][N:9]=1)[CH2:39][CH2:38][CH2:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 86640041Tert-butyl[4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl]carbamate

생성물 1

HCID 86640043Tert-butyl [4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl](3-phenylpropyl)carbamate수율 66%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of tert-butyl[4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl]carbamate (270 mg, 0.70 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in oil, 34 mg, 0.84 mmol) at room temperature, and the resulting mixture was stirred for 10 min. To this reaction mixture were added 3-phenylpropyl bromide (167 mg, 0.84 mmol) and potassium iodide (10 mg), and the mixture was further stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100) to give tert-butyl[4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-2-pyridyl](3-phenylpropyl)carbamate (232 mg, yield 66%) as a colorless oil.

후처리

  1. stirringthe mixture was further stirred at room temperature for 5 hr
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)

출처 및 근거

ORD 기록
ord-548b3a1a8afa48f6b3d26087bb434e5d
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492378B2

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