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CAS No. : | 122379-63-9 | MDL No. : | MFCD08272230 |
Formula : | C8H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DNIKOOPKCLWWPO-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 11240567 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.59 |
TPSA : | 37.91 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) : | -6.29 cm/s |
Log Po/w (iLOGP) : | 1.52 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.57 |
Log Po/w (MLOGP) : | 0.7 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.16 mg/ml ; 0.00786 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.68 |
Solubility : | 3.13 mg/ml ; 0.0211 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.02 |
Solubility : | 0.142 mg/ml ; 0.000959 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
58% | With n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; hexane; | Example 2 2-(1-Hydroxy-2-Phthalimidoethyl)-4-Methoxy-7-Azaindole (8b) Following the previous methodology, from <strong>[122379-63-9]4-methoxy-7-azaindole</strong> (3.55 g, 24 mmol) in THF (75 ml) n-BuLi (16.5 ml, 1.6 M in hexane), t-BuLi (16 ml, 1.7 M in hexane) and a solution of phthalimidoacetaldehyde (5 g, 26 mmol) in THF (100 ml) a crude mixture was obtained, which was purified by flash column chromatography. Elution with CH2Cl2/acetone (95/5) gave 4-methoxyazaindole (2.06 g, 58%) and with CH2C12/MeOH(98/2) afforded 8b (3.68 g, 43%) as a white solid. mp 225-226 C. (CH2Cl2/MeOH). IR (KBr) nu3500 (s, NH/OH), 1702 (s, C=O), 1594 (m), 1395 (m). 1H-NMR (DMSO-d6, 300 MHz) delta3.88 (s, 3H, Me), 3.86 (dd, J 13.8 and 6.0, 1H, H2'), 3.95 (dd, J 13.8 and 7.8, 1H, H2'), 5.00 (ddd, J7.8, 6.0 and 5.1, 1H, H1'), 5.73 (d, J5.1, 1H, OH), 6.30 (d, J 1.8, 1H, H3), 6.58 (d, J 5.4, 1H, H5), 7.83 (m, 4H, Phth), 8.02 (d, J 5.4, 1H, H6), 11.65 (br, 1H, NH). 13C-NMR (DMSO-d6, 75 MHz) delta43.6 (t, C2'), 55.3 (q, Me), 64.2 (d, C1'), 94.0 (d, C5), 97.8 (d, C3), 109.5 (s, C3a), 123.0 (d, Phth-P), 131.6 (s, Phth-ipso), 134.3 (d, Phth-alpha), 138.1 (s, C2), 144.2 (d, C6), 150.3 (s, C7a*), 158.5 (s, C4*), 167.7 (s, Phth-CO). MS (EI) m/z 338 (M+1, 4), 337 (M+, 20), 319 (M-H2O, 44), 177 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine;palladium-carbon; In ethanol; water; | A solution of 5,7-Dibromo-4-methoxy-7-azaindole 36 (680 mg, 2.22 mmol), 5% Pd/C (350 mg, 0.17 mmol) and hydrazine (2.5 mL, 80 mmol) in EtOH was heated at reflux for 1 h. The reaction mixture was allowed to cool to rt, filtered through celite and the filtrate concentrated. Aqueous NH4OH (11% in H2O, 45 mL) was added to the residue and the solution was extracted with CH2C2 (3*30 mL). The combined organics were dried (MgSO4), filtered and concentrated to yield 4-methoxy-7-azaindole 37 (290 mg, 1.95 mmol, 88%) as an orange solid. | |
With hydrazine;palladium-carbon; In ethanol; water; | A solution of 5,7-Dibromo-4-methoxy-7-azaindole 36 (680 mg, 2.22 mmol), 5% Pd/C (350 mg, 0.17 mmol) and hydrazine (2.5 mL, 80 mmol) in EtOH was heated at reflux for 1 h. The reaction mixture was allowed to cool to rt, filtered through celite and the filtrate concentrated. Aqueous NH4OH (11% in H2O, 45 mL) was added to the residue and the solution was extracted with CH2Cl2 (3*30 mL). The combined organics were dried (MgSO4), filtered and concentrated to yield 4-methoxy-7-azaindole 37 (290 mg, 1.95 mmol; 88%) as an orange solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Characterization of 36: 1H NMR (500 MHz, CDCl3) 8.73 (br s, 1H), 7.41 (dd, J=3.1, 2.8 Hz, 1H), 6.69 (d, J=3.1, 2.2 Hz, 1H), 4.13 (s, 3H); 13C NMR (125 MHz, CDC3) 146.6, 133.7, 128.8, 127.5, 120.2, 115.6, 101.9, 60.7. MS m/z (M+H)+calcd for C,H7Br2N2O: 304.88; found 304.88. HPLC retention time: 1.31 minutes (column A). Preparation of 4-methoxy-7-azaindole 37: | ||
Characterization of 36: 1H NMR (500 MHz, CDCl3) 8.73 (br s, 1H), 7.41 (dd, J=3.1, 2.8 Hz, 1H), 6.69 (d, J=3.1, 2.2 Hz, 1H), 4.13 (s, 3H); 13C NMR (125 MHz, CDCl3) 146.6, 133.7, 128.8, 127.5, 120.2, 115.6, 101.9, 60.7. MS m/z (M+H)+calcd for C8H7Br2N2O: 304.88; found 304.88. HPLC retention time: 1.31 minutes (column A). Preparation of 4-methoxy-7-azaindole 37: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | To MeOH (1 .5 L) was added Na (57 g, 2.48 mol) in portions over 2 h, and the mixture stirred to afford a clear solution. 4-methoxy-1 /-/-pyrrolo[2,3-b]pyridine (1-120) (64.4 g, 410 mmol) and tert-butyl 4-oxopiperidine-1 -carboxylate (165.0 g, 826 mmol) was added to the NaOMe solution (1 .5L) at 25 C. The reaction mixture was stirred at 80 C for 3 days. LCMS showed about 30% of starting material was remained. The reaction mixture was concentrated to remove MeOH. The residue was diluted into water (1 .5 L) and extracted with EtOAc/THF (2 x 1 .5 L/150 ml_). The extracts were washed with brine (2 x 2 L ). The extract was dried over Na2S04, and concentrated to give a residue (300 g), which was purified by silica gel chromatography (petroleum ether: EtOAc: THF = 3:1 :0.15 to 1 :1 : 0.15) to give te/ -butyl 4-(4-methoxy-1 H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (1-121) (49 g, 35%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium; at 140℃; for 44h;Autoclave; | To MeOH (600 mL) was added Na (22.6 g, 983 mmol.) in portions over 1 hr, and the mixture stirred to afford a clear solution. Then 4-chloro-1 /-/-pyrrolo[2,3-b]pyridine (1-119) (50 g, 327.69 mmol) was added. The reaction mixture was stirred at 140 C for 44 hr in a 1 L autoclave. Some yellow solids formed in the reaction mixture, and LCMS showed about 30% of starting material remained. The reaction mixture was concentrated under vacuum to remove MeOH. The residue was diluted into water (200 mL) and extracted with EtOAc/THF ( 2 x 300 mL/50 mL). The extracts were washed with saturated NH4CI (150 mL) and brine (150 mL). The extract was dried and concentrated to give a crude product, which was purified by silica gel chromatography (petroleum ether: EtOAc: THF = 3:1 :0.2 to 1 :1 : 0.2) and re-crystallized from petroleum ether/CH2CI2/EtOH (600 mL/100 mL/10 mL) to give 4-methoxy-1 H-pyrrolo[2,3-b]pyridine (1-120) (22 g, 45%) as a white solid. |
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