Sodium hydride → 5-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-3-methyl-[1,2,4]oxadiazole

HRID 2266406Notes

Reaction equation

HRID 2266406 reaction equation
[H-].[Na+].[OH:3][NH:4][C:5](=[NH:7])[CH3:6].C(O[C:11]([C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)[CH:17]=1)=O)C>C1COCC1>[Br:24][C:20]1[CH:19]=[C:18]([N:16]2[CH:17]=[C:13]([C:11]3[O:3][N:4]=[C:5]([CH3:6])[N:7]=3)[N:14]=[CH:15]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 161287541-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid ethyl esterHCID 178465666HCID 178465666, compound

Product 1

HCID 161285065-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-3-methyl-[1,2,4]oxadiazoleYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (1.30 g, 32.64 mmol, 60% in mineral oil) in THF (15 mL) under nitrogen atmosphere was added N-hydroxy-acetamidine (2.62 g, 35.4 mmol) and stirred for 1 h at room temperature. The bromo ester 3 (8 g, 27.2 mmol) in THF (2 mL) was added and refluxed for 12 h. The reaction mixture was quenched by adding brine, extracted with ethylacetate (100 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure and purified by flash chromatography using 25% ethylacetate in hexane as mobile phase to furnish 4 (2.8 g, 35%) as pale yellow solid, mp=200.1-202.4° C.

Workup

  1. temperaturerefluxed for 12 h
  2. customThe reaction mixture was quenched
  3. additionby adding brine
  4. extractionextracted with ethylacetate (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7d095b7ed0d04e27ae4723f3d4a3b101
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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