N-Iodosuccinimide → HCID 11134296, compound

HRID 277931Notes

Reaction equation

HRID 277931 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:22]=1)=[O:4].[I:25]N1C(=O)CCC1=O>CC#N>[F:24][C:2]([F:1])([F:23])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[I:25])=[O:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 12065950HCID 12065950, compound

Product 1

HCID 11134296HCID 11134296, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-trifluoroacetamido-6-benzoyl-imidazo[1,2-a]pyridine (2.0 g, 6.0 mmol) in 50 ml of dry CH3CN cooled at 0° C., was added N-iodosuccinimide (1.35 g, 6.0 mmol) portionwise. The mixture was stirred for 10 minutes. Acetonitrile was removed in vacuo and the residue was dissolved in EtOAc (250 ml), washed with NaHSO3 (40% p/v, 2×200 ml) and NaHCO3 (2×200 ml). The organic layer was dried (Na2SO4) and EtOAc was removed in vacuo to afford 2.60 g (95%) of product as a yellow solid. EIMS, NMR.

Workup

  1. customAcetonitrile was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (250 ml)
  3. washwashed with NaHSO3 (40% p/v, 2×200 ml) and NaHCO3 (2×200 ml)
  4. dry with materialThe organic layer was dried (Na2SO4) and EtOAc
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-3782df0bec6342739077b8181478c8db
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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