반응 #462591

반응 방정식

Pyrazolone

3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylmethyl]-1-cyclohexyl-5-pyrazolone

potassium carbonate

CH3I

→

3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylmethyl]-1-cyclohexyl-4,4-dimethyl-5-pyrazolone

용매

acetone

반응 조건

후처리

1. 1
   여과The reaction was filtered
2. 2
   기타solvent removed
3. 3
   기타The residue was chromatographed on silica gel

실험 절차

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).

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