1H-Indole-5-methanamine

5-Cyanoindole was hydrogenated over Raney Nickel in methanol with aqueous ammonia. The solution was concentrated under reduced pressure to a light yellow solid (C-(1H-indol-5-yl)-methylamine, 5.25 g, quantitative).To a stirring suspension of LiA1H4 (452 mg, 12.0 mmol) in THF (10 mL) was added asolution of 1H-indole-5-carbonitrile SM (994 mg, 7.0 mmol) in THF (8 mL) at 0 °C. The mixturewas warmed to 45 °C and stirred for 16 h. The reaction mixture was quenched with water (0.5 mL), 15percent NaOH( 0.5 mL) and then water (1.5 mL). The mixture was filtered and concentrated to obtain the residue, which was diluted with EtOAc (30 mL) and washed with water (10 mL) and then brine (10 mL). The organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue, which was washed with Et20 (15 mL) to afford (1H- indol-5-yl)methanamine compound 1 (790 mg, 79percent) as light yellow solid. ‘H NMR (300 MHz, DMSO-d6): 10.94 (s, 1H), 7.44 (s, 1H), 7.28 (d, J= 8.0 Hz, 1H), 7.04 (d, J 8.0 Hz, 1H), 6.34(s, 1H), 3.74 (s, 2H), 1.71 (s, 2H).Cyano derivative (N.ident.C-RIndole-5-methanamme (4).; To an ice-cold 1.0 M solution Of LiAlHTo a solution of lH-indole-5-carbonitrile (1.0 g, 7.0 mmol, 1.0 eq) in NLh/MeOH (10 mL) was added Raney Ni (about 100 mg). The suspension was hydrogenated at rt overnight. The mixture was filtered. The filtered cake was washed with MeOH (10 mL). The filtrate was concentrated under reduced pressure. The residue was purified via flash chromatography to afford (lH-indol-5-yl)methanamine as an off-white solid (330 mg, 32percent).

5-(AMinoMethyl)indole has been used as reactant for preparation of:• and HIV-1 integrase inhibitors targeting the catalytic domain and its ability for interaction with LEDGF/p751• 5-(Aminomethyl)indole is used in the synthesis of Vigabatrin (V253000) bioisosteres as inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT) inhibitors.

Molecular Weight:146.19
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:146.084398327
Monoisotopic Mass:146.084398327
Topological Polar Surface Area:41.8
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes