5192-04-1

Reactant for preparation of:• ;Fluorescent anion receptors and sensors1,2• ;Sulfate receptors3• ;Protein Kinase C θ (PKCθ) inhibitors4• ;Factor Xa Inhibitors5• ;Aurora kinase inhibitor• ;Antagonist of Mineralocorticoid Receptor6• ;Potent histone deacetylase (HDAC) inhibitors7• ;TRPV1 antagonists8• ;Derivatives of N-(7-indolyl)benzenesulfonamide as cell cycle inhibitors9

ChEBI: 1H-indol-7-amine is an indolamine.

The general procedure for the synthesis of 7-aminoindoles using 7-nitroindoles as starting material is as follows: 7-nitroindoles were dissolved in ethanol according to the method described in Scheme VII (step A). To this solution was added ammonium formate (10 equivalents) and a catalytic amount of 10% palladium carbon. Subsequently, the reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, it was cooled to room temperature, filtered through a diatomaceous earth pad to remove the catalyst, and the filtrate was concentrated under reduced pressure to give 7-aminoindole in purple solid form in 99% yield.

[1] Patent: WO2004/67529, 2004, A1. Location in patent: Page 75 - 76
[2] Patent: WO2005/92854, 2005, A1. Location in patent: Page/Page column 53
[3] Green Chemistry, 2017, vol. 19, # 3, p. 809 - 815
[4] Synthetic Communications, 2018, vol. 48, # 19, p. 2475 - 2484
[5] Patent: WO2005/92854, 2005, A1. Location in patent: Page/Page column 56-57