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CAS No. : | 189882-33-5 | MDL No. : | MFCD06659673 |
Formula : | C8H5N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GAFBPZMOMITHLG-UHFFFAOYSA-N |
M.W : | 143.15 | Pubchem ID : | 10534776 |
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) : | -6.21 cm/s |
Log Po/w (iLOGP) : | 1.22 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 1.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.19 |
Solubility : | 0.925 mg/ml ; 0.00646 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.06 |
Solubility : | 1.23 mg/ml ; 0.00862 mol/l |
Class : | 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 : | 1.64 |
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 |
---|---|---|
74% | With sodium hydroxide In ethanol at 90℃; for 18 h; | 1H-pyrrolo[2,3-b]pyridine-6-carbonitrile (120mg, 0.84mmol) was dissolved in ethanol (10ml). 6N Sodium hydroxide (1.4ml, 8.4mmol) was added, and the mixture was stirred for 18 hours at 90. The mixture was distilled under reduced pressure, and then 1N hydrochloric acid solution was added. The resulting solution 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 separated by column chromatography to obtain the title compound (100mg, 74percent). [945] NMR:1H-NMR(400HMz, DMS)-d 6); δ 12.08(brs, 1H),8.11(d, 1H), 7.83(d, 1H), 7.70(d, 1H), 6.58(d, 1H) |
176 g | With sodium hydroxide In ethanol at 80℃; | With 5 liters three bottles,Under mechanical agitation,123 g of 6-cyano-7-azaindole was added to 1.7 liters of ethanol,At room temperature,Add the concentration of 5N sodium hydroxide solution 1.2 liters,The temperature was kept at 80 ° C overnight,Thin layer chromatography TLC detection,To the raw material reaction completely,The reaction was stopped. Post-processing:After naturally dropping to room temperature, the reaction solution was poured into 5 liters of ice water and the pH was adjusted to 3 to 4 with hydrochloric acid to precipitate solidBody products, filtration, drying,be made of7-azaindole 6-carboxylic acid176 g.Sampling detection,High Pressure LiquidThe purity was 97percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triethylamine; In acetonitrile; for 72h;Reflux; | To a mixture of lH-pyrrolo[2,3- bjpyridine 7-oxide(3.0 g, 22.4 mmol) in MeCN were added TEA (5.6 g, 56 mmol) and TMSCN (13.2 g, 134 mmol) in five portions. The reaction mixture was stirred at reflux for 3 d then concentrated under reduced pressure. The residue was purified by column chromatography to give the desired compound (1.9 g, 60% yield) as yellow solid. LC-MS: m/z 144 (M+H)+. |
41 mg | With triethylamine; In acetonitrile; at 85℃; for 2h; | To a solution of the compound [96-1] obtained in the process (1) (360 mg) in acetonitrile (5 mL) were added triethylamine (0.75 mL) and trimethylsilyl cyanide (0.33 mL) at room temperature, and then the reaction mixture was stirred at 85C for 2 hours. To the reaction mixture was added aqueous solution of 1N-sodium hydroxide, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (41 mg) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 8.08 (1H, d, J = 8.1 Hz), 7.71 (1H, dd, J = 3.5, 2.6 Hz), 7.52 (1H, d, J = 8.1 Hz), 6.65 (1H, dd, J = 3.7, 2.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A: Phenyl(1H-pyrrolo[2,3-b]pyridin-6-yl)methanone In a round-bottomed flask under argon, 25.2 ml of 1M phenylmagnesium bromide in tetrahydrofuran are dissolved in 7 ml of anhydrous tetrahydrofuran. In another round-bottomed flask under argon, 0.6 g of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> and 1.07 ml of trimethylsilyl chloride are dissolved in 7 ml of tetrahydrofuran. That solution is then pipetted onto the magnesium solution at ambient temperature. After stirring for one night, the mixture is hydrolyzed with 20 ml of 2N ammonium chloride solution. The pH is then adjusted to 1 using 10% hydrochloric acid and the solution obtained is stirred for 2 hours at ambient temperature. The pH of the solution is adjusted to 9 using concentrated ammonium hydroxide solution and the aqueous phase is extracted twice with 20 ml of dichloromethane. The organic phases are dried over magnesium sulphate, filtered and evaporated under reduced pressure. After purification by chromatography on silica gel (pure dichloromethane and then dichloromethane/methanol:99/1), the title compound is obtained in the form of a yellow solid. Melting point: 174 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of lH-Pyitauolo[2,3-b]pyridine-6-carbonitrile (500 mg, 3.49 mmol) in THF (80 mL) was added Titanium (IV) isopropoxide (2.05 mL, 6.98 mmol) followed by EtMgBr (4.66 mL, 13.97 mmol) dropwise. The mixture was stirred at room temperature for 3 h. The dark color reaction mixture was quenched with 10 mL of H2O and stirred efficiently for 30 min. The resulting yellow suspension was filtered through a plug of celite, washed the celite cake with EtOAc followed by 10% MeOH/CH2Cl2. Solvents were removed and the resulting brown oil was suspended in Toluene (2x10 mL) to removed residual water. After evaporation of the solvent the crude amine products were obtained as a brownish solid. To a mixture of these crude amines and DIEA (801 uL, 4.60 mmol) in DCM (15 mL) was added BoC2O (810 mg, 3.71 mmol). The mixture was stirred at room temperature for 16 h. The reaction was diluted with DCM and washed with water, followed by Brine. Dried over MgSO4, filtered and concentrated down to provide crude material which was purified by silica gel chromatography (5% to 50% EtOAc in hexane) to give 80 mg of [1-(lH-Pyrrolo[2,3-&]pyridin-6-yl)-cyclopropyl]- carbamic acid tert-butyl ester (m/z 274.40 [M + I]+) and 230 mg of [1-(1H-Pyrrolo[2,3- b]pyridin-6-yl)-propyl]-carbamic acid tert-butyl ester m/z 276.41 [M + I]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A: Cyclopropyl(1H-pyrrolo[2,3-b]pyridin-6-yl)methanone In a round-bottomed flask under an argon atmosphere, 3 g (21 mmol) of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> are dissolved in 35 ml of anhydrous tetrahydrofuran. 5.35 ml (42 mmol) of trimethylsilyl chloride and 126 ml (126 mmol) of phenylmagnesium bromide (1M in tetrahydrofuran) are then added. The reaction mixture is stirred for 1 night at ambient temperature. It is then hydrolyzed with 100 ml of 2M ammonium chloride solution. The pH is then acidified to 1 using 10% hydrochloric acid and the mixture is stirred for 2 hours at ambient temperature. The pH of that solution is then brought to 9 using concentrated ammonium hydroxide solution. The aqueous phase is extracted twice with 100 ml of dichloromethane. The organic phases are dried over magnesium sulphate, filtered and evaporated under reduced pressure. The crude product is purified by chromatography on silica gel (petroleum ether/ethyl acetate: 9/1 then 8/2) to yield the title product in the form of a beige solid. Melting point: 159 C. MS: m/z=187 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A: 6-(1-Cyclohexylvinyl)-1H-pyrrolo[2,3-b]pyridine Under an argon atmosphere, 1.5 g (10.48 mmol) of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> are dissolved in 20 ml of anhydrous tetrahydrofuran. 2.66 ml (20.96 mmol) of trimethysilyl chloride are then added. That mixture is then added to 31 ml (62.87 mmol) of cyclohexylmagnesium chloride dissolved in 20 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred for 20 hours at ambient temperature. It is then hydrolyzed with 50 ml of 2M ammonium chloride. After acidification to pH 1 using 6M hydrochloric acid, the mixture is stirred for 2 hours at ambient temperature. It is then rendered basic to pH 8 using aqueous ammonium hydroxide solution and extracted 3 times with 20 ml of dichloromethane. The organic phases are dried over magnesium sulphate, filtered and evaporated. The crude product is purified by chromatography on silica gel (petroleum ether/ethyl acetate: 9/1, 8/2 then 7/3) to yield the title product in the form of a yellowish solid. Melting point: 160 C. MS: m/z=229 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Steps 1-3BzCI 1A7-azaindoline was sequentially treated with mCPBA (J. Org. Chem. 1980, 45, 4045), TMSCN/benzoyl chloride (Synthesis, 1992, 661) and LiOH (J. Agric. Food Chem. 1997, 45, 2345) to provide 6-cyano-7-azaindole 1A. The formation of compound 1 A is also described in the literature by alternate approaches (Synthesis 2008, 201 and Synthesis, 2008, 707). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Step 41A 1 BA solution of 1A (45 mg, 0.3 mmol) in THF (5 ml_) and DMF (1 ml_) was treated with NaHMDS (1 M/THF, 1.5mL) and stirred at RT for 30 min. NaI (45rng, 0.3 mmol) and 4-(chloromethyl)-1 -tritylimidazole (0.3g, 0.9mmol) were then added. The reaction was stirred overnight at RT and then concentrated. Chromatography (20-50% EtOAc/hex) provided 1 B (72 mg, 50%) and recovered starting material 1A (23 mg, 50%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 7-hydroxy-lH-pyrrolo[2,3-]pyridine (1.15 g, 8.57 mmol) in dry CH3CN (30 ml) was added isopropyl iodide (2.6 ml, 25.71 mmol) at RT. The mixture was stirred at 45 0C for about 40 h, before more isopropyl iodide was added (2.6 ml, 25.71 mmol). The mixture was further heated at 55 0C overnight. The solution was evaporated to dryness in vacuo. The residue was dissolved in sat. aq. NH4Cl (40 ml) and a solution, of potassium cyanide (1.12 g, 17.14 mmol) in water (10 ml) was added slowly at RT. The mixture was stirred at 45 0C overnight, then cooled to 4 0C in an ice bath, and sat. aq. NaHCO3 (30 ml) was added slowly. The mixture was stirred vigorously for Ih, then the precipitates were collected by filtration. The wet cake was rinsed with cold water and dried in vacuo to yield the title compound as an off-white solid. (HR-MS: 144.0568). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With zinc;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 140℃; for 4h;Inert atmosphere; | Acid-4: 3-Chloro-1 H-pyrrolo[2,3-b]pyridine-6-carboxylic acid; a) 1 H-Pyrrolo[2,3-b]pyridine-6-carbonitrile; To a mixture of 6-bromo-1 H-pyrrolo[2,3-b]pyridine (Synthesis, 1992, 661 , example 3b) (788 mg, 4 mmol), zinccyanide (329 mg, 2.80 mmol) and zinc dust (26.2 mg, 0.4 mmol) in dry DMF (12 ml) was added (dppf)PdCI2xCH2Cl2 adduct catalyst (163 mg, 0.2 mmol) under nitrogen. The mixture was heated at 140 C for 4 h. The reaction mixture was diluted with ethyl acetate and washed with aq. Saturated bicarbonate solution and brine, dried over sodium sulfate, filtered and evaporated. 1.04 g dark yellow oil. The crude product was chromatographed over silica gel (cyclohexane/ethyl acetate 3:1) to provide the title compound as a white solid.TLC Rf=0.35 (2: 1 cyclohexane:ethyl acetate);LC-MS: 0.81 min. (100% purity, ESI+ 144), API-ES+ 144;1H-NMR (400 MHz, CDCI3): delta 11.05 (s, 1 H, NH), 8.08 (d, 1 H), 7.71 (dd, 1 H), 7.52 (d, 1 H), 6.66 (m, 1 H). | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; zinc; In N,N-dimethyl-formamide; at 140℃; for 5h;Inert atmosphere; | A mixture of 6-bromo-1H-pyrrolo[2,3-b]pyridine (4.00 g, 20.30 mmol, 1.00 eq), Zn (132.75 mg, 2.03 mmol, 0.10 eq), Zn(CN)2(1.67 g, 14.21 mmol, 902.05 uL, 0.70 eq) and Pd(dppf)Cl2.CH2Cl2 (828.95 mg, 1.02 mmol, 0.05 eq) in DMF (10.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 140C for 5 h under N2 atmosphere. The reaction mixture was diluted with EtOAc (50 mL) and washed with aq. saturated bicarbonate solution (100 mL) and brine (100 mL*2), dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (SiO2, PE/EtOAc=10:1 to 3:1) to afford the title compound (1.50 g, 8.91 mmol, 43.88% yield, 85% purity) as a white solid. | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; zinc; In N,N-dimethyl-formamide; at 140℃; for 5h;Inert atmosphere; | A mixture of 6-bromo-lH-pyrrolo[2,3-b]pyridine (10 g, 50.75 mmol, 1 eq), Zn (331.88 mg, 5.08 mmol, 0.1 eq), Zn(CN)2 (4.17 g, 35.53 mmol, 2.26 mL, 0.7 eq) and Pd(dppf)Cl2.CH2Cl2 (2.07 g, 2.54 mmol, 0.05 eq) in DMF (100 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at l40C for 5 h under N2 atmosphere. It was diluted with water (500mL) and EtOAc (300mL), and then filtered to remove the solid, the solid was washed with EtOAc (200mLx2). The combined organic layers were washed with brine (500 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, PE/EtOAc = 5/1 to 2/1) to afford the title compound (5.3 g, 89% purity) as a green solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydroxide; In ethanol; at 90℃; for 18.0h; | <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> (120mg, 0.84mmol) was dissolved in ethanol (10ml). 6N Sodium hydroxide (1.4ml, 8.4mmol) was added, and the mixture was stirred for 18 hours at 90. The mixture was distilled under reduced pressure, and then 1N hydrochloric acid solution was added. The resulting solution 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 separated by column chromatography to obtain the title compound (100mg, 74%). [945] NMR:1H-NMR(400HMz, DMS)-d 6); delta 12.08(brs, 1H),8.11(d, 1H), 7.83(d, 1H), 7.70(d, 1H), 6.58(d, 1H) |
b) 1 H-Pyrrolo[2,3-b]pyridine-6-carboxylic acid; A suspension of 1 H-pyrrolo[2,3-b]pyridine-6-carbonitrile (690 mg, 4.82 mmol) in NaOH 2M (12 ml) was stirred at 100 C for 6 h. The reaction mixture was washed with diethyl ether and the aq. phase was set slightly acidic (pH 6-7) with cone. HCI. The solid formed was filtered off and dried to provide the title compound.LC-MS: RtH8= 0.51 min. (100% purity, ESI+ 163);1H-NMR (400 MHz, DMSO-D6): delta 12.78 (s, 1 H), 12.01 (s, 1 H), 8.08 (d, 1 H), 7.80 (m, 1 H), 7.73 (s, broad, unresolved, 1 H), 6.56 (s, broad, 1 H). | ||
176 g | With sodium hydroxide; In ethanol; at 80℃; | With 5 liters three bottles,Under mechanical agitation,123 g of <strong>[189882-33-5]6-cyano-7-azaindole</strong> was added to 1.7 liters of ethanol,At room temperature,Add the concentration of 5N sodium hydroxide solution 1.2 liters,The temperature was kept at 80 C overnight,Thin layer chromatography TLC detection,To the raw material reaction completely,The reaction was stopped. Post-processing:After naturally dropping to room temperature, the reaction solution was poured into 5 liters of ice water and the pH was adjusted to 3 to 4 with hydrochloric acid to precipitate solidBody products, filtration, drying,be made of7-azaindole 6-carboxylic acid176 g.Sampling detection,High Pressure LiquidThe purity was 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67 mg | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h; | To a solution of the compound [96-2] obtained in the process (2) (40 mg) in N,N-dimethylformamide (2 mL) were added potassium carbonate (82 mg) and 2,6-dimethylbenzyl chloride (69 mg) at room temperature, and then the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (67 mg) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.98 (1H, d, J = 7.8 Hz), 7.49 (1H, d, J = 8.1 Hz), 7.22 (1H, dd, J = 8.2, 7.0 Hz), 7.12 (2H, d, J = 7.6 Hz), 6.96 (1H, d, J = 3.4 Hz), 6.46 (1H, d, J = 3.7 Hz), 5.49 (2H, s), 2.27 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | To a mixture of AICI3 (2.2 g, 16.8 mmol) in anhydrous DCM (50 mL) at 0C was added acetyl chloride (2.1 g, 33.5 mmol). The mixture was stirred at r.t. for 1 hr, followed by addition of a solution of lH-pyrrolo[2,3-b]pyridine-6- carbonitrile (800 mg, 5.6 mmol) in anhydrous DCM (20 mL). The resulting mixture was stirred at r.t. for 2 hr then poured into ice -water and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford the desired product (500 mg, 50% yield). LC-MS: m/z 186 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[592] To a solution of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> (WO2011128455) (150 mg, 1.05 mmol) in THF (5.2 mL) at 0 C, was added NaH (60% in mineral oil, 46 mg, 1.15 mmol), and the reaction mixture was stirred for 30 minutes, warming to RT. chloromethyl methyl ether (MOM-Cl) (80 uL, 1.05 mmol) was added, and the reaction mixture was stirred at RT for 1 h, then quenched with sat. NaHCO3 (0.1 mL) and concentrated under reduced pressure. The residue was diluted with water (10 mL), extracted with DCM (3 x 10 mL), and the collected organics were washed with (1:1) water/NaHCO3 (2 x 10 mL) and brine (2 x 5 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (189 mg, 0.93 mmol, 87% yield) as a dark brown solid, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20℃; for 16h; | To a solution of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> (1.50 g, 10.48 mmol, 1.00 eq) in DCM (3.00 mL) was added NBS (2.24 g, 12.57 mmol, 1.20 eq) at 0C . The mixture was stirred at 20C for 16 h. It was concentrated. The residue was washed with PE (50 mL) and filtered to afford the title compound (3.00 g, 6.76 mmol, 64.46% yield, 50% purity) as a yellow solid. It was used for next step directly^ | |
With N-Bromosuccinimide; In dichloromethane; at 0 - 15℃; for 1h; | To a solution of lH-pyrrolo[2,3-b]pyridine-6-carbonitrile (4 g, 25.15 mmol, 1 eq) in DCM (40 mL) was added NBS (5.37 g, 30.18 mmol, 1.2 eq) at 0 C. The mixture was stirred at 15 C for 1 h. It was concentrated and the residue was washed with PE (500 mL) and the solid was filtered to afford the title compound (5 g, crude) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[588] To a solution of <strong>[189882-33-5]1H-pyrrolo[2,3-b]pyridine-6-carbonitrile</strong> (WO2011128455) (100 mg, 0.70 mmol) in THF (3.5 mL) at 0C, was added NaH (60% in mineral oil, 31 mg, 0.77 mmol), and the reaction mixture was stirred for 30 minutes, warming to RT. methyl iodide (46 uL, 0.73 mmol) was added, and the reaction mixture was stirred at RT for 1h, then concentrated under reduced pressure, diluted with MeTHF (10 mL) and water (5 mL) and extracted with MeTHF (2 x 5 mL). The organics were combined and washed with brine (2 x 5 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (114 mg, 0.70 mmol, quantitative yield) as a pale orange solid, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium carbonate; In ethanol; at 30℃; for 12h; | To a solution of lH-pyrrolo[2,3-b]pyridine-6-carbonitrile (1 g, 6.99 mmol, 1 eq) in EtOH (30 mL) was added NH2OH HCl (4.85 g, 69.86 mmol, 10 eq) and Na2C03 (8.89 g, 83.83 mmol, 12 eq). The mixture was stirred at 30 C for 12 h. The suspension was filtered and concentrated under reduced pressure to afford the title compound (1.3 g, crude) as yellow solid, which was used into the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.38% | With ammonium sulfide; In tetrahydrofuran; methanol; at 15℃; for 12h;Inert atmosphere; | To a solution of lH-pyrrolo[2,3-b]pyridine-6-carbonitrile (2 g, 13.97 mmol, 1 eq) in MeOH (20 mL) and THF (10 mL) was added ammonium sulfide (1.71 g, 25.15 mmol, 1.72 mL, 1.8 eq) at l5C. Then the solution was stirred at l5C for 12 h under N2 atmosphere. The solution was quenched by addition of H20 (30 mL) at l5C, and extracted with EtOAc (30 mLx2). The combined organic layers were washed with brine (20 mLx2), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, PE/EtOAc=30/l to 1/1) to afford the title compound (1 g, 5.64 mmol, 40.38% yield) as a yellow solid. (Note: The reaction was combined with another reaction (ET19050-19) in 1 g scale for purification and work up.) |
Tags: 189882-33-5 synthesis path| 189882-33-5 SDS| 189882-33-5 COA| 189882-33-5 purity| 189882-33-5 application| 189882-33-5 NMR| 189882-33-5 COA| 189882-33-5 structure
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P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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