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Butyl bromide → cis-4-[5-(3-Butoxymethylcyclopentyl)-[1,2,4]oxadiazol-3-yl]pyridine

HRID 221365
Notes
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Reaction equation

HRID 221365 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]=[C:10]([C@@H:12]3[CH2:16][CH2:15][C@H:14]([CH2:17][OH:18])[CH2:13]3)[O:9][N:8]=2)=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:22]([O:18][CH2:17][C@@H:14]1[CH2:15][CH2:16][C@H:12]([C:10]2[O:9][N:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:11]=2)[CH2:13]1)[CH2:23][CH2:24][CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 57954443HCID 57954443, compound

Product 1

HCID 66673905cis-4-[5-(3-Butoxymethylcyclopentyl)-[1,2,4]oxadiazol-3-yl]pyridine

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of cis-[3-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)cyclopentyl]methanol (Preparation 5, 40 mg, 0.116 mmol) in anhydrous THF (2 ml) was treated with sodium hydride (23 mg of a 60% dispersion in oil, 0.57 mmol) and tetrabutylammonium iodide (6 mg, 16 μmol). After stirring the mixture at rt for 10 min, 1-bromobutane (59 μl, 0.65 mmol) was introduced and stirring continued for 72 h. The solvent was removed in vacuo, the residue dissolved in CH2Cl2 (20 ml) and washed with water (2×5 ml). The organic phase was dried (MgSO4) and evaporated. Flash chromatography (IH-EtOAc, 7:3) afforded the title compound: RT=3.99 min, m/z (ES−)=302.3 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 72 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in CH2Cl2 (20 ml)
  5. washwashed with water (2×5 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-db1a0bd36df146ffbb7579609106a2cc
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes