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CAS No. : | 271-29-4 | MDL No. : | MFCD01686899 |
Formula : | C7H6N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLKDJOPOOHHZAN-UHFFFAOYSA-N |
M.W : | 118.14 | Pubchem ID : | 9219 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.09 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.07 |
Log Po/w (XLOGP3) : | 0.98 |
Log Po/w (WLOGP) : | 1.56 |
Log Po/w (MLOGP) : | 0.31 |
Log Po/w (SILICOS-IT) : | 2.15 |
Consensus Log Po/w : | 1.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 1.39 mg/ml ; 0.0118 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.17 |
Solubility : | 7.98 mg/ml ; 0.0675 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.86 |
Solubility : | 0.163 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.28 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
75% | With hydrogen In ethanol at 20℃; | A suspension of 7-chloro-1H-pyrrolo[2,3-c]pyridine (650 mg, 4.2 mmol) and Pd/C (10percent, 50 mg) in EtOH (25 mL) was stirred at RT under H2 atmosphere (balloon pressure). The reaction mixture was filtered through a celite pad, and the filter cake was washed with EtOAc (10 mL). The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH, 9/1/0.1), affording 1H-Pyrrolo[2,3-c]pyridine as a white solid (380 mg, 75percent yield). |
70.95% | With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 60 h; Inert atmosphere | To a solution of anhydrous THF (35.50 mL) was added 43 (0.71 g, 4.42 mmol). The resulting solution was degassed for 2 h using N2. Hereafter, PdCl2(dppf)*CH2Cl2 (180.50 mg, 0.22 mmol), TMEDA (2.25 mL, 15.03 mmol) and NaBH4 (0.57 g, 15.03 mmol) were added in sequence. The reaction was allowed to continue for 60 h at ambient temperature. The reaction was quenched by slowly pouring the solution in brine. After extraction with EtOAc ( .x. 3), the combined organic fractions were filtered over Hyflo Super Cel medium (calcined), concentrated in vacuo and purified using automated flash chromatography (EtOAc/MeOH/NH4OH, 960:37.5:2.5) to give 37 (0.39 g; 70.95percent yield). Note: This procedure was repeated multiple times using batches of 43 (0.25-2.5 g), giving consistent 65-75percent yields at reaction times of 14-60 h 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 8.04 (d, J = 5.5 Hz, 1H), 7.53-7.46 (m, 1H), 7.43 (t, J = 2.8 Hz, 1H), 6.64 (dd, J = 3.0, 2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydrogenchloride In tetrahydrofuran | c 1H-Pyrrolo[2,3-c]pyridine The azaindoline (step b, 1.1 g, 5.0 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 5.5M hydrochloric acid (5 ml). The mixture was heated at 50° C. for 4.5 hours cooled to 0° C. and basified with 5M sodium hydroxide (7.0 ml). The mixture was extracted with ethyl acetate (2*20 ml) and the combined ethyl acetate fractions were washed with saturated brine (20 ml), dried (Na2 SO4), filtered and concentrated in vacuo to afford the title compound as a pale yellow crystalline solid; yield: 0.57 g (97percent). mp. 132°-134° C.Lit. mp 131°-132°[C.]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | at 0 - 20℃; | To a solution of 1H-pyrrolo[2,3-c]pyridine (1 g, 8.47 mmol) in H2S04 (5 mL) was added 69percent HNO3 (533 mg, 8.47 mmol) at 0 °C. After stirred at 0 °C for 2 hrs, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was then poured into H20 (100 mL) and basified by NaOH powder to pH> 7. Then the mixture was extracted by EA (100 mL x3), dried over anhydrous Na2SO4, and evaporated in vacuum to afford 3-nitro-1H- pyrrolo[2,3-c]pyridine (690 mg, 50percent) as a yellow solid. ‘H NIVIR (400 IVIHz, DMSO-d6): ö = 8.94 (s, 1H), 8.85 (s, 1H), 8.44 (d, J= 5.2 Hz, 1H), 8.02 (dd, J= 5.6, 1.2 Hz, 1H). MS: m/z 164.0 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.295 g | With aluminum (III) chloride In nitromethane; 1,2-dichloro-ethane at 0℃; for 1 h; Inert atmosphere | To a solution of 1 /-/-pyrrolo[2,3-c]pyridine (0.400 g; 3.386 mmol) in a mixture of 1 ,2- dichloroethane (10 mL) and nitromethane (10 mL) cooled at 0 °C under an argon atmosphere were added dichloro(methoxy)methane (1.544 mL; 16.92 mmol) and aluminum trichloride (1.500 g; 1 1.25 mmol) over 1 h. After the addition, the reaction was quenched by addition of water and of a saturated sodium bicarbonate solution. The reaction mixture was extracted with a solution of dichloromethane and ethanol (9/1 , 6x100 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 0.295 g (60percent) of 1 H-pyrrolo[2,3-c]pyridine-3-carbaldehyde which was used without further purification. ESI/APCI(+): 147 (M+H). ESI/APCI(-): 145 (M-H). 1H NMR (DMSO- ofe) δ 10.01 (1 H, s); 8.88 (1 H, s); 8.50 (1 H, s); 8.33 (1 H, d); 8.00 (1 H, d). |
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