Methyl 4-(bromomethyl)-3-methoxybenzoate → methyl 4-[5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate

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The starting indole (C) was prepared according to the procedure of Example 1, starting with 5-(N-cyclopentylmethylcarbamoyl)indole (A) and methyl 4-bromomethyl-3-methoxybenzoate (B) to yield methyl 4-[5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate (C) (1.14 g, 33%) as a tan foam; partial NMR (80 MHz, CDCl3): 3.45(dd, 2H, CH2N), 3.93(s, 3H, OCH3), 3.95(s, 3H, OCH3), 4.17(s, 2H, ArCH2), 6.17(t, 1H, NHCO), 7.01(d, 1H, H2 -indole), 7.16(d, 1H), 8.04(br s. 1H, H4 -indole), 8.45(br s, 1H, NH).

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