1-Methyl-1H-indol-5-amine

Brown solid

10percent Pd/C (0.18 g/g of startingmaterial) was added to a solution of starting material dissolved inTHF (54 mL/g of starting material). Reaction flask was sealed andvacuum was used to remove air. A balloon filled with hydrogen gaswas then attached to the flask. The reaction was stirred at roomtemperature for 24e48 h or until disappearance of starting materialwas observed by TLC. The reaction was then filtered through celite.Filtrate was rotovapped to give a brown solid; 100percent; 1H NMR(DMSO): δ 7.15-7.05 (m, 2H), 6.71 (dd, J 3.0, 0.9 Hz, 1H), 6.57 (dd, J 8.5, 2.1 Hz, 1H), 6.12 (dd, J 3.0, 0.9 Hz, 1H), 3.67 (s, 3H); 13CNMR (DMSO): δ141.30, 131.12, 129.49, 129.44, 129.41, 112.31, 110.11, 104.21, 99.13, 32.86.1-Methyl-5-nitro -1H- indole (270mg, 1mmol), Fe powder (1.12g, 20mmol, 10equiv) was added ethanol (15ml) and glacial acetic acid (2ml) in, 78 heated at reflux for 1h, TLC monitoring. After completion of the reaction, it was filtered through Celite, washed with ethanol to precipitate a colorless, ethanol rotary evaporation. The solid was dissolved in ethyl acetate followed by the addition, ultrasonic minutes, extracted with saturated NaHCOA2 (1.0 g, 5.7 mmol) was dissolved in ethanol and catalyzed with Pd/C and H2 for 5 hours at 50°C. The catalyst was filtered off and the solvent was removed to give 0.85 g of A3. The yield in this step was 95.5percent without further purification.General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.Step G: Synthesis of 1 -methyl- lH-indol-5 -amine as an intermediate To l-methyl-5-nitro-lH-indole (0.5g, 2.84mmol) in ethyl acetate (10ml), tin (II) chloride hydrate (2.5g, 11.4mmol, 4eq) was added and the reaction mixture stirred overnight at room temperature. The reaction mixture was basified with aqueous sodium EPO General procedure: A solution of the compound IV (1.0 eq) with aniline derivatives (1.0 eq) and camphor sulfonic acid (0.4 eq) in isopropanol was stirred at reflux for 6 h. The solvent was evaporated under vacuum, and the crude residue was purified by silica gel column chromatography eluted with a mixture of dichloromethane and methanol.General procedure: (+)-Usnic acid (1 equiv.) and primary ammonia compounds (1.1 equiv.) were added in absolute EtOH under nitrogen and the reaction mixture was stirred at 80C for 4h. For the hydrochloride salt materials, they (1.1 equiv) were added to absolute ethanol, and an equivalent amount of pyridine (1.1 equiv) was added dropwise thereto and stirred at 80C under nitrogen. After 5min, (+) - usnic acid was added and the reaction mixture was stirred for another 4h. After reaction was complete, the reaction solution was cooled and concentrated under reduced pressure. The residues were quickly purified by silica gel column (PE/EtOAc).

Molecular Weight:146.19
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:146.084398327
Monoisotopic Mass:146.084398327
Topological Polar Surface Area:31
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes