N-Iodosuccinimide → 2-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

HRID 1043656Notes

Reaction equation

HRID 1043656 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:4][CH:3]=1.[I:17]N1C(=O)CCC1=O>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[C:14]([I:17])[N:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 673361162-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 673357762-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazoleYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole (0.6 g, 2.55 mmol) was dissolved in N,N-dimethylformamide (10 mL) and N-iodosuccinimide (0.63 g, 2.81 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight in the absence of light. The yellow suspension was filtered and rinsed with diethylether (2×2 mL) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.65 g, 71%). The filtrate was evaporated and the residue was triturated with diethylether (6 mL) and filtered. This solid was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0:10 to 1:9) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.15 g, 16% yield).

Workup

  1. filtrationThe yellow suspension was filtered
  2. washrinsed with diethylether (2×2 mL)

Sources & evidence

ORD record
ord-cdcd5fb59e744bbaadba6bad0d80bda9
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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