81881-74-5

5-(Aminomethyl)indole is used in the synthesis of Vigabatrin (V253000) bioisosteres as inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT) inhibitors.

Reactant for preparation of:• ;HIV-1 integrase inhibitors targeting the catalytic domain and its ability for interaction with LEDGF/p751• ;Inhibitors of Gli1-mediated transcription in the Hedgehog pathway2• ;SCIO-469-like compounds for the inhibition of p38 MAP kinase3• ;4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase c theta (PKC θ) inhibitors4• ;Non-covalent thrombin inhibitors5

The hydrogenation reaction was carried out using Raney Nickel as a catalyst in a methanol solution containing ammonia with 5-cyanoindole as starting material. After completion of the reaction, the reaction solution was concentrated under reduced pressure to give a light yellow solid product, C-(1H-indol-5-yl)-methylamine (5.25 g, quantitative yield).

[1] Patent: US2004/204455, 2004, A1. Location in patent: Page/Page column 18
[2] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4991 - 5002
[3] Patent: US2003/153596, 2003, A1
[4] Patent: WO2016/44770, 2016, A1. Location in patent: Page/Page column 584; 585
[5] Patent: WO2011/76784, 2011, A2. Location in patent: Page/Page column 66