N-Iodosuccinimide → 3-Iodo-7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).