Methyl iodide → HCID 11747380, compound

HRID 1078259Notes

Reaction equation

HRID 1078259 reaction equation
[CH2:1]([CH:4]1[C:13]2[NH:12][C:11](=[O:14])[CH:10]=[CH:9][C:8]=2[CH2:7][C:6]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:5]1)[CH:2]=[CH2:3].I[CH3:20]>C(Cl)(Cl)Cl>[CH2:1]([CH:4]1[C:13]2[N:12]=[C:11]([O:14][CH3:20])[CH:10]=[CH:9][C:8]=2[CH2:7][C:6]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 15336554HCID 15336554, compound

Product 1

HCID 11747380HCID 11747380, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of Ag2CO3 (7.17 g, 26.2 mmol), pyridone 3 (5.4 g, 21.9 mmol), and iodomethane (8.0 mL, 131 mmol) in 200 mL of CHCl3 was refluxed in the dark with stirring. After cooling, filtration, and concentration, the residue was purified by flash chromatography with 25% ethyl acetate in hexanes as the eluent to afford 5.14 g (90%) of 4a: IR (neat) 2953, 1589, 1487, 830 cm-1 ; 1H NMR δ7.22 (d, 1H, J=8.2 Hz), 6.52 (d, 1H, J=8.2 Hz), 5.80 (m, 1H), 5.03 (m, 2H), 4.01 (m, 4H), 3.89 (s, 3H), 3.11 (m, 1H), 2.96 (m, 2H), 2.80 (dd, 1H, J=16.0, 2.4 Hz), 2.50 (m, 1H), 2.06 (m, 1H), 1.80 (dd, 1H, J=13.2, 10.9 Hz); 13C NMR δ162.0, 154.5, 139.7, 137.1, 121.6, 116.3, 108.1, 107.9, 64.5, 64.4, 53.1, 39.4, 38.1, 38.0, 36.6; MS m/z 261 (M+), 246, 220, 174, 148.

Workup

  1. temperaturewas refluxed in the dark
  2. temperatureAfter cooling
  3. filtrationfiltration, and concentration
  4. customthe residue was purified by flash chromatography with 25% ethyl acetate in hexanes as the eluent

Sources & evidence

ORD record
ord-b08aaeb7f8d244a09b50b3cbb9b96679
Source dataset
uspto-grants-1996_08
Patent number
US05547960

Reaction notes

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