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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
Notes
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Reaction equation

HRID 452763 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-548b3a1a8afa48f6b3d26087bb434e5d
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492378B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes