Methyl iodide → HCID 15293291, compound

HRID 375409Notes

Reaction equation

HRID 375409 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]3[NH:21][N:22]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)[C:23](=O)[CH:24]=3)=[C:9]2[CH3:32])=[O:7])=[CH:4][CH:3]=1.[C:35](=[O:38])([O-])[O-].[K+].[K+].[CH3:41]I>CC(C)=O>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]3[C:24]([CH3:41])([CH3:23])[C:35](=[O:38])[N:22]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)[N:21]=3)=[C:9]2[CH3:32])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18995258HCID 18995258, compound

Product 1

HCID 15293291HCID 15293291, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Pyrazolone from Example 9 (300 mg, 0.62 mmol) was dissolved in dry acetone (5 mL) to which was added anhydrous potassium carbonate (100 mg, 0.7 mmol) and CH3I (500 mg, 3 mmol). The reaction was stirred at room temperature for 5 hours under nitrogen. The reaction was filtered and solvent removed under reduce pressure. The residue was chromatographed on silica gel. The title compound elutes with 25% EtOAc/hexane. 1H-NMR (CDCl3) δ=7.67 (d, 2H, J=8.49 Hz), δ=7.49 (d, 2H, J=8.43 Hz), δ=6.93 (d, 1H, J=2.37 Hz), δ=6.84 (d, 1H, J=5.61 Hz), δ=6.69 (dd, 1H, J=2.43, 8.91 Hz), δ=4.05 (m, 1H), δ=3.81 (s, 3H), δ=3.78 (s, 2H), δ=2.40 (s, 3H), δ=1.9 (d, 6 H), δ=1.83-1.45 (m, 10H); 13C-NMR (CDCl3) δ=171.77, 168.65, 156.89, 156.34, 135.77, 133.56, 131.73, 130.63, 129.52, 115.38, 114.09, 112.07, 101.24, 56.05, 52.56, 40.81, 31.44, 27.40, 25.93, 25.74, 13.62; LRMS (FAB) 506.4 (M+H+); Rf 0.6 (EtOAc/hexanes 1:1).

Workup

  1. filtrationThe reaction was filtered
  2. customsolvent removed
  3. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-02b51634bece4b41aacdd977bcbaa717
Source dataset
uspto-grants-1996_01
Patent number
US05484940

Reaction notes

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