Potassium Carbonate → HCID 66845912, compound

HRID 1696314Notes

Reaction equation

HRID 1696314 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=[C:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH:18]1(I)[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:18]1([N:7]2[C:2](=[O:1])[C:3]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:6]2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 66844842HCID 66844842, compound

Product 1

HCID 66845912HCID 66845912, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylate (Step 2, 210 mg, 0.91 mmol), cyclopentyl iodide (196 mg, 1.0 mmol) and potassium carbonate (150 mg, 1.1 mmol) were stirred at room temperature in 2 mL of DMF for 24 h. The reaction mixture was quenched with H2O and extracted 3× with EtOAc. The combined organic extracts were washed 3× with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was taken up in CH2Cl2 and loaded on to a 5 g pre-packed silica gel column and purified. Elution with 0-30% EtOAc:hexanes gave the title compound as an off-white powder (57 mg, 21%). MS m/z: 299 (M+1).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic extracts were washed 3× with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified
  8. washElution with 0-30% EtOAc

Sources & evidence

ORD record
ord-88a6595e0c4144f882a74fad40227c1c
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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