N-bromobutanimide → 3-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide

HRID 383304Notes

Reaction equation

HRID 383304 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])=[CH:6][C:5]=12.C1C(=O)N([Br:27])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:27][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 684844493-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

Product 1

HCID 684844313-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide (1 eq, 0.398 mmol, 100 mg) is dissolved in DMF (4 ml) at 0° C. and NBS (1.1 eq, 0.438 mmol, 77.9 mg) is added. The reaction mixture is stirred for 1 h at 0° C. and then 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-(3-bromo-imidazo[1,2-a]pyridin-7-yl)-N-methyl-benzamide as a brown solid; [M+H]+=331

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-9300777925ea4c60acc496568dbdab59
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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