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CAS No. : | 29906-67-0 | MDL No. : | MFCD07772841 |
Formula : | C9H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PXBQSCHRKSBGKV-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 147322 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.02 |
TPSA : | 50.75 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.53 cm/s |
Log Po/w (iLOGP) : | 1.75 |
Log Po/w (XLOGP3) : | 1.19 |
Log Po/w (WLOGP) : | 2.09 |
Log Po/w (MLOGP) : | 0.7 |
Log Po/w (SILICOS-IT) : | -0.28 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.13 |
Solubility : | 1.31 mg/ml ; 0.00744 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.85 |
Solubility : | 2.48 mg/ml ; 0.0141 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.22 |
Solubility : | 1.05 mg/ml ; 0.00598 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
100% | With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; | 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. |
95.8% | With iron; acetic acid In ethanol at 78℃; for 1 h; | 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 NaHCO3 wash, water, NaCl wash, saturated MgSO4 dry. The organic layer by rotary evaporation, dried, the crude product was purified by column chromatography to give 230mg of yellow product, 1-methyl-5-amino-1H- indole, yield 95.8percent. |
95.5% | With palladium on activated charcoal; hydrogen In ethanol at 50℃; for 5 h; | A2 (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. |
81% | With hydrazine hydrate In ethanol at 80℃; for 1 h; Inert atmosphere | 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. |
77% | With hydrogen In tetrahydrofuran; ethanol for 4 h; | Step G: Synthesis of 1 -methyl- lH-indol-5 -amine as an intermediate <n="38"/>; [0100] A mixture of l-methyl-5-nitro-lH-indole (2.00 g, 11.3 mmol) and platinum (IV) oxide (0.20 g, 10percent by weight) in a mixture of ethanol (20 mL) and tetrahydrofuran (20 mL) was shaken under an atmosphere of hydrogen at 40 psi for 4 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure. Purification by flash chromatography (silica, 1 :3, ethyl acetate/hexanes) afforded 1-methyl- lH-indol-5-amine (1.28g, 77percent) as a red oil: 1H NMR (500 MHz, CDCl3) δ 7.12 (d, J= 8.5 Hz, IH), 6.95 (d, J= 3.0 Hz, IH), 6.92 (d, J= 2.0 Hz, IH), 6.69 (dd, J= 2.0, 8.5 Hz, IH), 6.28 (d, J= 3.0 Hz, IH), 3.72 (s, 3H), 3.47 (bs, 2H). |
27% | With tin(ll) chloride In ethyl acetate at 20℃; | 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 <DP n="50"/>hydroxide solution (pH 8) and the compound extracted using ethyl acetate. The crude compound obtained was purified by column chromatography over silica gel using ethyl acetate/ hexane (1:1) as eluent to give 1 -methyl- lH-indol-5ylamine (120mg, 27percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1 h; Stage #2: at 20℃; |
Step F: Synthesis of l-methyl-5-nitro-lH-indole as an intermediate; [0099] To a mixture of 5-nitro-lH-indole (5.0 g, 30.8 mmol) in λ/,λf-dimethylformamide (100.0 mL) was added sodium hydride (60percent in mineral oil, 1.35 g, 33.9 mmol), and the mixture stirred for 1 h at room temperature. After this time, iodomethane (2.11 mL, 33.9 mmol) was added, and the mixture was stirred at room temperature overnight. After this time, saturated aqueous ammonium chloride (100 mL) was added and the organics extracted with ethyl acetate (150 mL). The organics were then washed with 5percent aqueous lithium chloride (200 mL), water (200 mL) and brine (1000 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford l-methyl-5-nitro-lH-indole (5.42 g, 100percent) as an orange/brown solid: 1H NMR (500 MHz, CDCl3) δ 8.59 (d, J= 2.0 Hz, IH), 8.13 (dd, J = 2.0, 9.0 Hz, IH), 7.34 (d, J= 9.0 Hz, IH), 7.20 (d, J= 3.0 Hz, IH), 6.67 (dd, J= 0.5, 1.0, 3.0, 3.5 Hz, IH), 3.86 (s, 3H). |
100% | Stage #1: With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1 h; Stage #2: at 20℃; |
Dissolve A1 (10.0 g, 61.7 mmol) in 100 ml of N,N-dimethylformamide.A tetrahydrofuran suspension of NaH (2.7 g, 112.5 mmol) was slowly added dropwise and reacted for 1 hour at room temperature. 4.3 ml of methyl iodide was added and the reaction was stirred overnight at room temperature. After the reaction was completed, it was washed with 1 L of saturated ammonium chloride solution and extracted with 500 ml of ethyl acetate to obtain an organic layer. Then, 400 ml of a 5percent lithium chloride solution, 1 L of water, and 1 L of brine are successively washed, and the organic layer is added with anhydrous magnesium sulfate. After drying overnight, the solvent was removed to obtain 10.9 g of A2. The yield of this step was 100percent, which was completely converted into the target product. |
92% | With potassium hydroxide In acetone at 0℃; for 10 h; Heating / reflux | To a solution of 5 -nitro-1 H-indole (2.Og, 12.3mmol) in acetone (20ml), powdered potassium hydroxide (3.4g, 60.7mmol, 5eq) was added followed by the addition methyl iodide (2.6 Ig, 18.5mmol, 1.5eq) at O0C. The reaction mixture was heated to reflux for 10 hr. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the organic layer was concentrated to dryness to yield l-methyl-5 -nitro-1 H-indole (2.Og, 92percent). The crude compound was used in the next stage without purification. |
47.5% | With potassium carbonate In acetonitrile at 80℃; | The 5-nitroindole (972mg, 6mmol), K2CO3 (1.66g, 7.2mmol) was dissolved in acetonitrile (20ml), a 80 °C was heated at reflux for several hours, until TLC monitored the reaction. After rotary evaporation and then, solid was dissolved in ethyl acetate, added saturated NH 4Cl solution and extracted. The organic layers were combined, spin crude done. Finally, the product was purified by column to give the intermediate 1-methyl-5-nitro-indole -1H- 769mg. Yield 47.5percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.1% | With potassium carbonate In n-heptane; ethyl acetate; N,N-dimethyl-formamide | Example 14 Synthesis of 1-methyl-5-nitroindole. A 500 mL, three-necked flask equipped with a thermocouple, condenser, and addition funnel was charged with 5-nitroindole (20.0 g, 12.3 mmol), potassium carbonate (4.0 g, 29 mmol), N,N-dimethylformamide (80 mL) and dimethyl carbonate (22 mL, 26.14 mmol). The resulting mixture was heated to reflux. The reaction was monitored by HPLC or TLC (solvent system: 30percent ethyl acetate in heptane). An analysis of the reaction mixture after 3 h at reflux, by the above methods, failed to detect any remaining 5-nitroindole. The reaction mixture was then cooled to 10+-5° C. and diluted with water (160 mL) which resulted in the formation of a yellow precipitate. After the mixture was stirred at room temperature for 2 h, the solid was collected by filtration, then was washed with water (100 mL) and dried under high vacuum at 60-65° C. for 24 h to give 1-methyl-4-nitroindole (21.1 g, 97.1percent) as a yellow solid. |
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