N-Iodosuccinimide → HCID 86721405, compound

HRID 869567Notes

Reaction equation

HRID 869567 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[CH:12]=1.[I:13]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[I:13][C:12]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 3435423HCID 3435423, compound

Product 1

HCID 86721405HCID 86721405, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 3] To 2-(methoxymethyl)imidazo[1,2-a]pyridine (1.8 g, 11 mmol) obtained in step 2 were added DMF (22 mL) and N-iodosuccinimide (2.75 g, 12 mmol), and the mixture was stirred at room temperature for 3 hr. The reaction was discontinued with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate and the extract was dried over sodium sulfate. Filtration, concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=10/1 v/v) gave 3-iodo-2-(methoxymethyl)imidazo[1,2-a]pyridine (3.1 g, 99%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over sodium sulfate
  3. filtrationFiltration, concentration
  4. customunder reduced pressure and purification by silica gel column chromatography (chloroform/methanol=10/1 v/v)

Sources & evidence

ORD record
ord-4b25587d1e1549f4aae5eca1c43906ab
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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