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CAS No. : | 27257-15-4 | MDL No. : | MFCD09743451 |
Formula : | C8H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZVOCBNCKNQJAFL-UHFFFAOYSA-N |
M.W : | 132.16 | Pubchem ID : | 583068 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.0 |
TPSA : | 17.82 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) : | -6.21 cm/s |
Log Po/w (iLOGP) : | 1.78 |
Log Po/w (XLOGP3) : | 1.26 |
Log Po/w (WLOGP) : | 1.57 |
Log Po/w (MLOGP) : | 1.32 |
Log Po/w (SILICOS-IT) : | 1.49 |
Consensus Log Po/w : | 1.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.0 mg/ml ; 0.0076 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.23 |
Solubility : | 7.73 mg/ml ; 0.0585 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.44 |
Solubility : | 0.483 mg/ml ; 0.00366 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.17 |
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% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere Stage #2: for 1 h; Inert atmosphere |
General procedure: The preparation of the known compound 1a: A dried round-bottomed flask equipped with a magnetic stirring bar was charged with 7-azaindole (2 g, 16.95 mmol) and DMF (10 mL) under a nitrogen atmosphere. The mixture was cooled to 0 °C, NaH (1.2 equiv) was added and stirring continued for 1 h. Then, methyl iodide (1.1 equiv) was added and the mixture was stirred for another 1 h. Afterwards the reaction was quenched with ice cold water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure to give N-methyl-7-azaindoles in a quantitative yield [3]. |
96% | Stage #1: With Tris(3,6-dioxaheptyl)amine; potassium <i>tert</i>-butylate In toluene at 0 - 20℃; for 3 h; Stage #2: at 0 - 20℃; for 1 h; |
General procedure: To a cold solution of appropriate pyrrolo-pyridines 8a,c,e (2.5 mmol) in anhydrous toluene (25 mL), t-BuOK (0.38 g, 3.4 mmol) and TDA-1 (1 or 2 drops) were added at 0 °C. The reaction mixture was stirred at room temperature for 3 h and then MeI (2.5 mmol, 0.2 mL) was added at 0 °C. TLC analysis (ethyl acetate) revealed that methylation was complete after 1 h. The solvent was evaporated under reduced pressure. The residue was treated with water, extracted with DCM (3 × 20 mL), dried (Na2SO4), evaporated and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent to give derivatives 8b,d,f [42]. |
85% | Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5 h; Stage #2: at 20℃; |
a) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine; lH-Pyrrolo [2, 3-b] pyridine (1.00 g, 8.46 mmol) was dissolved in 10 mL of DMF and cooled on an ice bath. NaH (0.203 g, 8.47 mmol) was added and after 30 min methyl iodide (0.527 mL, 8.47 mmol) was added. The reaction mixture was stirred overnight at room temperature and then poured into 100 mL of water, extracted three times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated and a clean product was obtained. Yield: 0.950 g (85percent). 'H NMR (300 MHz, CDC13) 88. 34 (dd, 1H), 7.90 (dd, 1H), 7.18 (d, 1H), 7.05 (dd, 1H), 6.45 (d, 1H), 3.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h; Stage #2: for 1 h; |
To a solution of lH-pyrrolo[2,3-b]pyridine (1.00 g, 8.46 mmol)and DMF (10 mL) is added 60percent NaH (0.41 g, 10.16 mmol). After 30 min, MeI (0.63 mL, 10.16 mmol) is added and the solution stirred for 1 h. The solution is diluted with EtOAc (60 mL), washed with water (2 X 50 mL), brine (50 mL), dried aver MgSO4, filtered and concentrated to furnish the title compound (1.10 g, 0.83 mmol, 99percent). 1H NMR (CDCl3), δ 3.90 (s, 3H), 6.45 (d, J = 3.5 Hz, IH), 7.05 (dd, 7 = 8.1, 4.6 Hz, IH), 7.17 (d, J = 3.5 EPO <DP n="65"/>Hz, IH), 7.90 (d, J = 7.7, 1.8 Hz, IH), 8.40 (dd, J = 4.8, 1.3 Hz, IH). LC/MS (m/z): calcd. for C8H8N2 (M+H)+: 133.2; found:. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: at 0℃; for 0.166667 h; Stage #2: at 0 - 60℃; for 1.51667 h; Stage #3: With sodium hydrogencarbonate In water |
b) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine-3-carbaldehyde; POC13 (1.2 g, 7.9 mmol) was added dropwise with stirring to 10 mL of DMF at 0°C. After stirring 10 min a solution of 1-methyl-lH-pyrrolo [2, 3-b] pyridine (0.95 g, 7. 2 mmol) in 5 mL of DMF was added during 1 min. The reaction mixture was stirred for lh at 0°C and a further 30 min at 60°C. It was poured into water which was made alkaline with NaHC03 (aq) and extracted 3 times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product (0.85 g, 74percent) was sufficiently pure to be used in the subsequent step below. 'H NMR (300 MHz, CDC13) No. 9. 97 (s, 1H), 8.55 (m, 1H), 8.44 (m, 1H), 7.84 (s, 1H), 7.27 (m, 1H), 3.97 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube | General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydrogencarbonate; trichlorophosphate In ethyl acetate; N,N-dimethyl-formamide | (Step 2) Synthesis of 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde Phosphoryl chloride (5.15 ml, 55.3 mmol) was added dropwise to DMF (70 ml) under stirring at 0OEC. After the reaction mixture was stirred at 0OEC for 10 minutes, a solution of 1-methyl-1H-pyrrolo(2,3-b)pyridine (4.87 g, 36.8 mmol) in DMF (5 ml) was added dropwise at the same temperature. After completion of the dropwise addition, the reaction mixture was stirred at 0OEC for 4 hours and at 60OEC for 3.5 hours. The reaction mixture was poured in ice water - a saturated aqueous solution of sodium bicarbonate to neutralize the mixture therewith, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde (4.87 g, 83percent) was obtained as a yellow solid. 1H-NMR (CDCl3) δ: 3.98 (s, 3H), 7.28 (dd, J=7.8,4.7Hz, 1H), 7.85 (s, 1H), 8.44 (d, J=4.7Hz, 1H), 8.55 (d, J=7.8Hz, 1H), 9.97 (s, 1H). MS (ESI) m/z 160 (M+-H). |
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