Hydrochloric Acid → [1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

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Reaction Conditions

Reaction Steps

A stirred solution of N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide (2.215 g, Example 25) in tetrahydrofuran (55 ml) was treated with a solution of phenylmagnesium chloride in tetrahydrofuran (9.83 ml, 2M). The solution was stirred at 0° C. for 2 hours then poured into a mixture of ice and 1N hydrochloric acid (10 ml) and then partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.05 g) as a yellow solid, m.p. 146-147° C. [Elemental analysis:— C, 80.80; H, 6.00; N, 3.80%. Calculated for C24H21NO2:— C, 81.10; H, 5.96; N, 3.94%].

Provenance & Evidence