HCID 20746075, compound → HCID 20746058, compound

Participants

Reaction Steps

To a stirred solution of 2-methyl-5-nitro-indole-1-carboxylic acid methylamide (0.65 g, 2.78 mmol) in 20 mL EtOAc and 4 mL EtOH was added Pd on C (0.3 g, 10% w/w). The mixture was stirred under H2 balloon at room temperature for one hour and filtered through a pad of silica gel. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography eluting with 1-3% MeOH in CH2Cl2 to give 140 mg 5-amino-2-methyl-indole-1-carboxylic acid methylamide (24% yield) together with 150 mg 5-amino-2-methyl-2,3-dihydro-indole-1-carboxylic acid methylamide (26% yield). 1H NMR (300 MHz, CD3OD) δ 7.56 (d, 1H, J=6.2 Hz), 6.65 (s, 1H), 6.58 (d, 1H, J=6.1 Hz), 4.41 (m, 1H), 3.23-3.39 (m, 1H), 2.85 (s, 3H), 2.54 (d, 1H, J=15.5 Hz), 1.20 (d, 3H, J=6 Hz).

Provenance & Evidence