ETHYL2-AMINOINDOLE-3-CARBOXYLATE

Off-White Crystalline Solid

Step 2. Synthesis of ethyl-2-amino-lH-indol-3-carboxyate [formula 12-3]Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65°C for one day. Then Zn was deleted with celite filtering, and AcOH was removed under the reduced pressure to obtain solid product. The obtained solid was dissolved in excess dichloromethane, and then hexane was added to yield the title compound (6 g, 44percent).Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200 mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65° C. for one day. 3.3. Ethyl 2-amino-5-chloro-1H-indole-3-carboxylate (7) : Compound 7 was prepared according to modified literature conditions.Crude 5 (60 g, 221 mmol) was dissolved in glacial acetic acid (600 ml) and zinc dust (40 g) was added after parts during 45 min. The mixture was stirred for 2 h without external heating (reaction is exothermic, temperature in the flask reached 55°C during reaction) and filtered through a pad of cellite. The pad was washed with acetic acid (400 ml) and solution was evaporated. The residue was then washed well with water and dried under reduced pressure. Compound 7 (46.1 g, 88percent) was obtained as brown powder and further purified by column chromatography (hexane/chloroform, 0–60percent chloroform); mp: 190–193°C. 1H NMR is in agreement with literature.Crude material was used directly for the next step. 3.4. Ethyl 2-amino-1H-indole-3-carboxylate (8) : Compound 8 was prepared as described for 7 from crude 6 (44.2 g), product 8 (33.1 g, 86percent) was obtained as brown powder. 1H NMR is in agreement with literature. Crude material was used directly for the next step.

Molecular Weight:204.22
XLogP3:2.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:204.089877630
Monoisotopic Mass:204.089877630
Topological Polar Surface Area:68.1
Heavy Atom Count:15
Complexity:245
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes