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CAS No. : | 873055-09-5 | MDL No. : | MFCD22689954 |
Formula : | C12H14N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | COQNCAZGNLRPHM-UHFFFAOYSA-N |
M.W : | 218.25 | Pubchem ID : | 57470196 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 66.39 |
TPSA : | 61.61 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.08 cm/s |
Log Po/w (iLOGP) : | 2.22 |
Log Po/w (XLOGP3) : | 3.59 |
Log Po/w (WLOGP) : | 3.37 |
Log Po/w (MLOGP) : | 2.39 |
Log Po/w (SILICOS-IT) : | 1.49 |
Consensus Log Po/w : | 2.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.74 |
Solubility : | 0.0398 mg/ml ; 0.000182 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.57 |
Solubility : | 0.00587 mg/ml ; 0.0000269 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.88 |
Solubility : | 0.0286 mg/ml ; 0.000131 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20.0℃; for 2.5h;Heating / reflux; | To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). 1H NMR (300 MHz, CDCl3) delta 8.30 (br. s, 1H), 8.29 (s, 1H), 8.00 (dd, J=2.1, 8.7 Hz, 1H), 7.53 (d, J=9.3 Hz, 1H), 6.38 (s, 1H), 1.43 (s, 9H). |
80% | With bunazosin; In 1,4-dioxane; | 2-tert-Butyl-6-nitro-1H-indole To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). |
80% | With bunazosin; In 1,4-dioxane; | 2-tert-Butyl-6-nitro-1H-indole To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). 1H NMR (300 MHz, CDCl3) delta 8.30 (br. s, 1H), 8.29 (s, 1H), 8.00 (dd, J=2.1, 8.7 Hz, 1H), 7.53 (d, J=9.3 Hz, 1H), 6.38 (s, 1H), 1.43 (s, 9H). |
80% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20.0℃; for 2.5h;Reflux; | To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). |
80% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 2.5h;Reflux; | To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With hydrogen;nickel; In methanol; at 20.0℃; under 760.051 Torr; for 3.0h; | To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Nickel (0.2 g). The mixture was hydrogenated under 1 atm of hydrogen at room temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue washed with petroleum ether to give 2-tert-butyl-1H-indol-6-amine (1.0 g, 89%). 1H NMR (300 MHz, DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); MS (ESI) m/e (M+H+) 189.1. |
89% | In methanol; | B-6; 2-tert-Butyl-1H-indol-6-ylamine To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 m/z (MH+). |
89% | With hydrogen;Raney Ni; In methanol; at 20.0℃; for 3.0h; | To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 ink (MH+). |
89% | With Raney Ni; In methanol; at 20.0℃; under 760.051 Torr; for 3.0h; | To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 m/z (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With hydrogen; In methanol; | 2-tert-Butyl-1H-indol-6-amine To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Nickel (0.2 g). The mixture was hydrogenated under 1 atm of hydrogen at room temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-amine (1.0 g, 89%). 1H NMR (300 MHz, DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); MS (ESI) m/e (M+H+) 189.1. |