1,1-Dimethylethyl 5-amino-1H-indole-1-carboxylate

To a solution of tert-butyl 5-nitro-1H-indole-1-carboxylate (525 mg, 2.0 mmol) in ethyl acetate (8 ml) was added 10percent palladium on carbon (50 mg). Stir overnight at room temperature in a hydrogen atmosphere. Suction filteration, The filtrate was evaporated under reduced pressure to give a white solid (469 mg, 100percent)Pd/C (DeGussa catalyst) (1.5 g) was added to a suspension of 5-nitro-indole-1-carboxylic acid tert-butyl ester (4.77 g) in EtOH (100 mL) at room temperature and the reaction mixture was stirred under hydrogen atmosphere (balloon pressure) for 6 hours. 2 (100 mg, 0.38 mmol), ETOH:H20 (1;1, 5 mL), Fe powder (3 eq), NH4C1 (5 eq), mixed at RT then raised to 80°C. After 2 h, a polar product was observed by TLC. The reaction was quenched with ice cold water and extracted with EtOAc (2X10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by silica gel column chromatography [using 100-200 mesh, eluting with 15percent EtOAc-hexanej to afford 50 mg of 3. Repeat preparation with 500mg of 2 yielded 250 mg of 3.

Molecular Weight:232.28
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:232.121177757
Monoisotopic Mass:232.121177757
Topological Polar Surface Area:57.2
Heavy Atom Count:17
Complexity:298
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes