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CAS No. : | 517918-95-5 | MDL No. : | MFCD06659684 |
Formula : | C8H5N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRAQIXNADYAISI-UHFFFAOYSA-N |
M.W : | 143.15 | Pubchem ID : | 11788355 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.81 |
TPSA : | 52.47 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) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 1.2 |
Log Po/w (XLOGP3) : | 1.03 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.98 |
Solubility : | 1.49 mg/ml ; 0.0104 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.72 |
Solubility : | 2.72 mg/ml ; 0.019 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.97 |
Solubility : | 0.153 mg/ml ; 0.00107 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
83% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 36 h; Inert atmosphere | 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile A solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (5.0 g, 25.0 mmol, 1.0 eq.), Zn(CN)2 (3.6 g, 20.0 mmol, 0.8 eq.) in dry DMF (65 mL) was deoxygenated with a stream of argon for 30 min and then Pd(Ph3P)4 (1.7 g, 1.5 mmol, 0.06 eq.) was added. The reaction mixture was heated at 80° C. for 36 h then quenched with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and evaporated to dryness. The residue was treated with small amount of CH2Cl2 and filtered. The collected precipitate was rinsed with CH2Cl2 and dried on air to give 1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (Intermediate 2a) as a white solid (3.0 g; yield: 83percent; UPLC purity: 100percent). |
75% | at 80℃; | 1H-Pyrrolo [2,3-b]pyridine-5-carbonitrile (35) 24 35 A mixture of bromide 24 (10.0 g, 50.8 mmol), ZnCl2 (3.58 g, 30.5 mmol), and Pd (PPh3) 4 (3.52 g, 3.05 mmol) in DMF (110 mL) was heated at 80 C overnight. The solvent was evaporated and the residue separated by silicagel chromatography (100 g column) using hexane: ethyl acetate as eluent (gradient elution). The resulting solid was partitioned between water (200 ML)/CH2CL2 (100 mL) and the aqueous phase extracted with more CH2C12 (4 x 100 mL). The combined organic extracts were dried (MGSO4) and concentrated to give the product as a white solid (5. 48 g, 75percent), which was used for subsequent reactions without further purification. |
73% | at 110℃; for 4.5 h; | Preparation Example R-6. 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile 5-Bromo-1H-pyrrolo[2,3-b]pyridine described in Preparation Example R-5 (90mg, 0.46mmol), zinc cyanide (80mg, 0.69mmol) and tetrakis(triphenylphosphine)palladium(0) (53mg, 46μmol) were dissolved in N-methyl-2-pyrrolidinone (2mL), and the mixture was stirred for 4.5 hours at 110°C under nitrogen atmosphere. The reaction mixture was cooled to room temperature, water and ethyl acetate were added to the reaction mixture, the organic layer was partitioned, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1), and the title compound (48mg, 0.34mmol, 73percent) was obtained as a white solid. 1H-NMR Spectrum (DMSO-d6) δ (ppm) 6.55-6.68(1 H, m), 7.65-7.78 (1 H, m), 8.52 (1 H, s), 8.60 (1 H, s), 12.3 (1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | at 80℃; | 1H-Pyrrolo [2, 3-b] pyridine-5-carbonitrile (2); A mixture of bromide 1 (10.0 g, 50.8 mmol), ZnCl2 (3.58 g, 30.5 mmol), and Pd (PPh3) 4 (3.52 g, 3.05 mmol) in DMF (110 mL) was heated at 80 °C overnight. The solvent was evaporated and the residue separated by silicagel chromatography (100 g column) using hexane: ethyl acetate as eluent (gradient elution). The resulting solid was partitioned between water (200 mL)/CH2Cl2 (100 mL) and the aqueous phase extracted with more CH2C12 (4 x 100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give product 2 as a white solid (5.48 g, 75percent), which was used for subsequent reactions without further purification. |
73% | at 110℃; for 4.5 h; | 5-Bromo-1H-pyrrolo[2,3-b]pyridine described in Preparation Example R-5 (90mg, 0.46mmol), zinc cyanide (80mg, 0.69mmol) and tetrakis(triphenylphosphine)palladium(0) (53mg, 46μmol) were dissolved in N-methyl-2-pyrrolidinone (2mL), and the mixture was stirred for 4.5 hours at 110°C under nitrogen atmosphere. The reaction mixture was cooled to room temperature, water and ethyl acetate were added to the reaction mixture, the organic layer was partitioned, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 5 : 1), and the title compound (48mg, 0.34mmol, 73percent) was obtained as a white solid. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 6.55-6.68(1H, m), 7.65-7.78 (1 H, m), 8.52 (1 H, s), 8.60 (1 H, s), 12.3 (1 H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | at 125℃; for 48 h; | To a solution of 5-Bromo-7-azaindole XXX (300 mg, 1.52 mmol) in DMF (10 ml), sodium cyanide (150 mg, 3.06 mmol), cuprous iodide (45 mg, 0.24 mmol), and Tetrakis (triphenylphosphine) palladium(0) (100 mg, 0087 mmol) were added. The reaction was placed under argon heated at 125° C. for 48 hours after which the reaction was allowed to cool to ambient temperature before diluting with ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (2.x., 150 ml). The organic layers were then combined and washed with saturated bicarbonate solution (3.x., 100 ml), before drying over sodium sulfate and evaporate under reduced pressure. The crude material was purified by preparative TLC, eluting with a solution of 70percent hexane, 30percent ethyl acetate with triethylamine as an additive to yield the titled compound as an off-white solid. (150 mg, M-1=142.0) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | at 100℃; for 12 h; Inert atmosphere | Step 1: Preparation of 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0748) (0749) A mixture of 1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (500 mg, 3.50 mmol) and concentrated HCl (3.6 mL) in H2O (18 mL) was stirred at 100° C. for 12 hours. The resulting mixture was cooled to room temperature. The solid thus obtained was washed with water to give the title compound (337 mg, 29percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: With sodium hydroxide In ethanol at 100℃; for 72 h; Stage #2: at 0℃; |
The compound obtained from Preparation Example 121 was dissolved in ethanol (100ml), and 6N sodium hydroxide (17ml, 102mmol) was added thereto. The mixture was stirred for 3 days at 100 and then distilled under reduced pressure. 1 N hydrochloride solution was added and the residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and the residue was dissolved in tetrahydrofuran (400ml). 0.25M solution of diazomethane in diethyl ether (30ml, 7.5mmol) was slowly added dropwise. The mixture was stirred for 30 minutes at 0 and then distilled under reduced pressure to obtain the title compound (1.2g, 67percent). |
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