HCID 58172079, compound → HCID 58172076, compound

Participants

Reaction Steps

5-Nitro-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (prepared by the procedure described in Example 2 for the 5-bromo analog) (426 mg) was dissolved in 20 mL of methanol. Palladium on carbon (85 mg) was added and the flask was seal with a rubber septum. A vacuum was pulled through a needle and the void was refilled from a balloon of hydrogen gas. The resulting mixture was stirred under 1 atm of hydrogen gas for 17 h. In the morning, LCMS analysis revealed consumption of the starting material and formation of the product. The reaction mixture was filtered through diatomaceous earth and concentrated under vacuum to yield 5-amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester as an orange foam (432 mg, solvent trapped within). This material was used without further manipulation.

Provenance & Evidence