N-Iodosuccinimide → (4-Fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine

HRID 1043661Notes

Reaction equation

HRID 1043661 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:13][C:12]3=[N:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:4][CH:3]=1.[I:17]N1C(=O)CCC1=O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16]([I:17])[N:11]3[N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67335853(4-Fluoro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl-amine

Product 1

HCID 67334575(4-Fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Fluoro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl-amine (0.117 g, 0.50 mmol) was suspended in N,N-dimethylformamide (3 mL) and N-iodosuccinimide (0.124 g, 0.55 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 2 hours in the absence of light. The mixture was evaporated and the residue was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.4:9.6 to 1:9) to give 0.13 g of (4-fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine as an off-white solid (72% yield).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.4:9.6 to 1:9)

Sources & evidence

ORD record
ord-5cc5c995a92d475b9a893fb0c7a6576d
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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