Methyl iodide → 2-Methyl-1-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanone

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Reaction Steps

Lithium diisopropylamine mono(tetrahydrofuran) (1.5M in cyclohexane, 11.5 ml) was added dropwise to a cold (-70°) solution of 1-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanone (8.8 g) in dry THF (175 ml) under nitrogen. The stirred solution was allowed to warm to 20° over 1 h then cooled to -70°. Iodomethane (2.15 ml) was added and the mixture was allowed to reach 20° over 1 h and stirred for a further 2 h. More iodomethane (1.08 ml) was added and stirring was continued for 2 h. The mixture was treated with acetic acid (10 ml) and water (10 ml), poured into saturated potassium carbonate solution (200 ml) and extracted with ethyl acetate (2×100 ml). The combined, dried organic extracts were filtered and evaporated to give a yellow foam (11.3 g). FCC (column made up of EtOAc:Et3N 99:1) eluting with ethyl acetate gave the title compound (5.0 g) as a white solid, m.p. 209°-210°.

Provenance & Evidence