N-bromobutanimide → 3-Bromo-7-chloroimidazo[1,2-a]pyridine

HRID 383298Notes

Reaction equation

HRID 383298 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:18][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]2=[N:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 196959017-Chloroimidazo(1,2-a)pyridine

Product 1

HCID 467391183-Bromo-7-chloroimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

7-Chloro-imidazo-[1,2-a]-pyridine (1 eq, 38.9 mmol, 5.93 g) is dissolved in DMF (20 ml) at 0° C. and NBS (1.1 eq, 42.8 mmol, 7.61 g) is added. The reaction mixture is stirred for 1 h at 0° C. and is diluted with EtOAc. The reaction mixture is washed with NaHCO3 and brine, dried over MgSO4, filtered and evaporated. The product is purified by flash column chromatography eluting with 8:2 DCM/MeOH to afford 3-bromo-7-chloro-imidazo-[1,2-a]-pyridine as a brown solid; [M+H]+=232

Workup

  1. washThe reaction mixture is washed with NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by flash column chromatography
  6. washeluting with 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-01a95fab00f84eef93eab8aa5a019c69
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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