Cesium carbonate → Benzyl 1-(cyclopropylmethyl)-5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

HRID 1725632Notes

Reaction equation

HRID 1725632 reaction equation
[CH:1]1([CH2:4]Br)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16](=[O:19])[NH:17][CH:18]=1>CN(C)C=O.O>[CH:1]1([CH2:4][N:17]2[CH:18]=[C:13]([I:12])[CH:14]=[C:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:16]2=[O:19])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

Product 1

HCID 68958794Benzyl 1-(cyclopropylmethyl)-5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamateYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cyclopropylmethyl bromide (0.100 mL, 0.99 mmol) and cesium carbonate (0.323 mg, 0.99 mmol) were added to a solution of benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate (0.245 g, 0.66 mmol) in dimethylformamide (3 mL) and stirred overnight. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by chromatography (silica gel, 10% to 50% ethyl acetate in hexanes gradient elution) gave the title compound (0.190 g). MS 425 (M+1)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby chromatography (silica gel, 10% to 50% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-54a1a11f62ba497882ae9e02a63f3047
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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