N-bromobutanimide → N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

HRID 556311Notes

Reaction equation

HRID 556311 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]([F:25])([F:24])[C:11]([NH:13][C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]2[CH:23]=1)=[O:12]>C(#N)C>[Br:1][C:23]1[N:17]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]2=[N:15][C:14]=1[NH:13][C:11](=[O:12])[C:10]([F:24])([F:9])[F:25]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 251966492,2,2-Trifluoro-N-(6-fluoroimidazo[1,2-a]pyridin-2-yl)acetamide2×

Product 1

HCID 57607463N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (2.96 g, 0.0166 mol) was added to a solution of 2,2,2-Trifluoro-N-(6-fluoro-imidazo[1,2-a]pyridin-2-yl)-acetamide (compound c, 3.74 g, 0.0151 mol) in acetonitrile (70 mL) and stirred at room temperature. The reaction mixture was stirred at room temperature for 15 minutes. Reaction mixture was concentrated under reduced pressure, crude product taken up in ethyl acetate, washed with water, organic layer collected, dried over Na2SO4, concentrated in vacuo and crude product purified by column chromatography (50% ethyl acetate/hexanes) to give product as an off white solid. Rf 0.47, 50% ethyl acetate/hexanes; MS m/z 327 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure, crude product
  4. washwashed with water, organic layer
  5. customcollected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo and crude product
  8. custompurified by column chromatography (50% ethyl acetate/hexanes)
  9. customto give product as an off white solid

Sources & evidence

ORD record
ord-f40c06f565014580a6f2446f15e46029
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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