N-Iodosuccinimide → 3-Iodo-7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridine

HRID 1446661Notes

Reaction equation

HRID 1446661 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]3[CH:17]=[CH:18][N:19]=[C:13]3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1C(=O)N([I:27])C(=O)C1>CC#N>[I:27][C:17]1[N:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=3)=[CH:12][C:13]2=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 68543695Imidazo[1,2-a]pyridine,7-[4-(methylsulfonyl)phenyl]-

Product 1

HCID 685436593-Iodo-7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treat a solution of 7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridine (101 g, 371.3 mmol, 1 eq) in 2000 mL of CH3CN at 0° C. with NIS (83.5 g, 371.3 mmol, 1 eq). Allow the mixture to stir at room temperature for 1 hour. Remove the solvent and the dissolve the residue in 5000 mL of CH2Cl2, wash with 10% NaOH solution, NaHSO3 sat., water and aqueous saturated sodium chloride. Dry over MgSO4 and evaporate. Triturate the solid obtained with hexanes, filter and dry in vacuo to afford 110 g of the title compound as a yellow solid. (Yield: 75%). MS (ES), m/z 399 (M+1).

Workup

  1. customRemove the solvent
  2. dissolutionthe dissolve the residue in 5000 mL of CH2Cl2
  3. washwash with 10% NaOH solution, NaHSO3 sat., water and aqueous saturated sodium chloride
  4. dry with materialDry over MgSO4
  5. customevaporate
  6. customTriturate the solid
  7. customobtained with hexanes
  8. filtrationfilter
  9. customdry in vacuo

Sources & evidence

ORD record
ord-545681c161f9498abf7082bb81d42ec7
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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