N-Iodosuccinimide → HCID 86710085, compound

HRID 1468280Notes

Reaction equation

HRID 1468280 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]3([CH3:14])[CH2:13][CH2:12]3)[N:10]=[C:6]2[CH:5]=[C:4]([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[CH:3]=1.[I:22]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[I:22][C:8]1[N:7]2[C:2]([CH3:1])=[CH:3][C:4]([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])=[CH:5][C:6]2=[N:10][C:9]=1[C:11]1([CH3:14])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 86710086HCID 86710086, compound

Product 1

HCID 86710085HCID 86710085, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Butyl 5-methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-7-carboxylate (370 mg, 1.29 mmol) obtained in step 1 was dissolved in DMF (3.0 mL), and the solution was stirred at room temperature for 3 hours after adding N-iodosuccinimide (320 mg, 1.42 mmol). Then, a saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL). The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20) to give butyl 3-iodo-5-methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-7-carboxylate (351 mg, yield 66%).

Workup

  1. filtrationthe mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL)
  2. customThe solvent was then evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-855d71f57d5e4973ad5a1ec55999287e
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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