Methyl iodide → 1-(5-chloro-1-methyl-1H-indol-2-yl)heptan-1-one

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[H-].[Na+].I[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:22])[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

Komponenten

Versuchsvorschrift

To a solution of the title compound of Example 1 Step B (98.0 mg, 0.37 mmol) in DMF was added NaH (15.0 mg, 60% suspension in mineral oil, 0.37 mmol). After 10 min, iodomethane (0.023 mL, 0.37 mmol) was added, and the mixture was stirred for 2 h, whereupon it was quenched by addition of sat. aq. NaHCO3. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 10%, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS C, tr=2.78 min, m/z 278.3 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.65 (app t, J=1.0 Hz, 1H), 7.31 (d, J=1.0 Hz, 2H), 7.20 (s, 1H), 4.05 (s, 3H), 2.95 (t, J=7.0 Hz, 2H), 1.79-1.72 (m, 2H), 1.43-1.26 (m, 6H), 0.90 (t, J=7.5 Hz, 3H).