N-bromobutanimide → 3-Bromo-7-thiazol-2-yl-imidazo[1,2-a]pyridine

HRID 1446669Notes

Reaction equation

HRID 1446669 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]2[CH:12]=[CH:13][N:14]=[C:8]2[CH:7]=1.C1C(=O)N([Br:22])C(=O)C1>C(O)C.ClCCl>[Br:22][C:12]1[N:9]2[CH:10]=[CH:11][C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[CH:7][C:8]2=[N:14][CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 685434347-Thiazol-2-yl-imidazo[1,2-a]pyridine

Product 1

HCID 685397873-Bromo-7-thiazol-2-yl-imidazo[1,2-a]pyridineYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 7-thiazol-2-yl-imidazo[1,2-a]pyridine (1.14 g, 5.66 mmol) in 25 mL absolute ethanol, then add NBS (1.0 g, 5.66 mmol), stir the mixture at room temperature for 15 minutes, dilute with 35 mL dichloromethane and apply to a 10 g SCX Mega Bond-Elut™ cartridge (Varian) pre-washed with 150 mL 1:1 CH2Cl2:MeOH. Wash the SCX cartridge with 300 mL 1:1 CH2Cl2:MeOH, elute with 150 mL CH2Cl2:2 M NH3-MeOH, and concentrate the eluates and dry to provide 1.07 g (67%) of the title compound as a tan solid. MS (ES) 280, 282.

Workup

  1. washpre-washed with 150 mL 1:1 CH2Cl2
  2. washWash the SCX cartridge with 300 mL 1:1 CH2Cl2
  3. washMeOH, elute with 150 mL CH2Cl2
  4. concentration2 M NH3-MeOH, and concentrate the eluates
  5. customdry

Sources & evidence

ORD record
ord-21a2d8e681ab4c06a3299f810d10953b
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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