Isopropyl iodide → HCID 58550769, compound

HRID 1908116Notes

Reaction equation

HRID 1908116 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C.C(#N)C>[CH:19]([N:3]1[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]1=[O:1])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 58550769HCID 58550769, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 2-oxo-1H-pyridine-4-carboxylate (700 mg, 4.57 mmol) in dry DMF (4.4 mL) was added finely ground K2CO3 (2.53 g, 18.3 mmol) followed by 2-iodopropane (914 μL, 9.14 mmol). The mixture was heated at 60° C. (external) for 1 h. The mixture was diluted with acetonitrile (10 mL) and was filtered. The filtrate was evaporated onto Celite and was purified by column chromatography (0-100% EtOAc/DCM) to give methyl 1-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylate (230 mg). ESI-MS m/z calc 195.1. found 196.3 (M−1)−. Retention time: 1.09 minutes (3 min run).

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated onto Celite
  3. customwas purified by column chromatography (0-100% EtOAc/DCM)

Sources & evidence

ORD record
ord-1ae2c3b379c04734882ad128e1572e40
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

Loading…