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CAS No. : | 581-50-0 | MDL No. : | MFCD00006215 |
Formula : | C10H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEKIYFGCEAJDDT-UHFFFAOYSA-N |
M.W : | 156.18 | Pubchem ID : | 11389 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.47 |
TPSA : | 25.78 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) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 1.46 |
Log Po/w (WLOGP) : | 2.14 |
Log Po/w (MLOGP) : | 0.91 |
Log Po/w (SILICOS-IT) : | 2.55 |
Consensus Log Po/w : | 1.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.4 |
Solubility : | 0.619 mg/ml ; 0.00396 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.61 |
Solubility : | 3.85 mg/ml ; 0.0247 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -4.16 |
Solubility : | 0.0109 mg/ml ; 0.00007 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
88% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 100℃; for 3h; | Pd2 (dba)3 (1.129 g, 1.233 mmol), S-Phos(2.025 g, 4.93 mmol), pyridin-3-yl boronicacid (8.34 g, 67.8 mmol), and potassium phosphate (26.2 g,123 mmol) were combined in a flask, degassed by vacuum/backfill, then a degassed mixture of dioxane (205 ml) and water (103 ml) wasadded via cannula, and 2-chloropyridine(5.79 ml, 61.6 mmol) was added via syringe. The mixture was heated at 100 C. for 3 hours andcooled to room temperature. Brine and EtOAc were added and, after separation, the aqueous layer was extracted three times with EtOAc. Thecombined organic layers were washed with brine, dried, the solvent was removed, and residue was coated on celite. Column chromatographyyielded a yellow oil that was distilled under vacuum (bath: 200 C. vapor: 162 C.), yielding 8.50 g (88%) of colorless oil. |
>= 99%Chromat. | With potassium carbonate;sodium tetrachloropalladate(II); (9-ethyl-2-sulfofluorenyl)dicyclohexyl-phosphonium-tetrafluoroborate; In water; at 45 - 100℃; for 14h;Product distribution / selectivity; | (ii) Suzuki reaction of aryl halides (in water) Preparation of the catalyst-stock-solution: The catalyst stock solution was prepared as described for the aqueous Sonogshira reaction using 9-Et-2-SO3HFlu-PCy2-HBF4 (13a). Cross-coupling reaction: Aryl halide (1 mmol), boronic acid (1.2 mmol) and K2CO3 (3.2 mmol) were first added to water (4 ml), then the catalyst stock solution and two drops of Labrasol (caprylocaproyl macrogol-8 glyceride blend, saturated polyglycolized glycerides consisting of mono-, di-and triglycerides of mono- and di-fatty acids of polyethylene glycol (PEG)) were added. The reaction mixture was stirred at the respective temperatures (see Table 8) for 0.5-20 h (see Table 8). After cooling to room temperature the reaction mixture was diluted with ether (15 ml), washed with water (10 ml), the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was isolated by column chromatography (silica, cyclohexane / ethylacetate (100:2). Alternatively the yield was determined via gas chromatography with hexadecane or diethylene glycol di-n-butylether as an internal standard. |
General procedure: Catalyst (2 mol%), aryl halide (1 equiv.) and Na2CO3 (1.1 equiv.) were stirred in H2O (5 mL) taken in the round bottom flask. The aryl boronic acid (1.1 equiv.) was added to the stirring solution. Stirring was continued for required time at 45 C. After the requisite time, the reaction mixture was diluted with water and the product was extracted with ethyl acetate. The ethyl acetate extract was passed through celite bed and then analyzed by GC. Authentic samples of both reactant and product were used to verify the retention time and to confirm the product formation. The ethyl acetate extract was concentrated and chromatographed on a silica gel column using hexane and ethylacetate as eluent to afford coupled product. The products are characterized by NMR, GC MS and UPLC analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Example 3 Synthesis of 2,3'-bipyridine Tetrahydrofuran (10 ml) and isopropylmagnesium chloride (2.0 M, 8.2 ml, 16.4 mmol) were charged in a nitrogen-substituted flask having an inner volume of 50 ml and then a solution obtained by dissolving 3-bromopyridine (2.59 g, 16.4 mmol) in tetrahydrofuran (3 ml) was added dropwise over 10 min. The reaction mixture was stirred for 1 hr, and a solution obtained by dissolving 2-benzenesulfonylpyridine (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred at room temperature for 5 hr, and isopropanol (1 ml) was added to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.65 g, yield 91% based on 2-benzenesulfonylpyridine) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) delta: 7.23-7.58 (m, 2H), 7.70-7.91 (m, 2H), 8.33-8.39 (m, 1H), 8.62-8.88 (m, 2H), 9.20 (d, 1H, J=3.0 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.3% | EXAMPLE 2 Synthesis of 2,3'-dipyridyl (A-2) The same synthesis procedures as in Example 1 were conducted except for using 3-cyanopyridine in place of 4-cyanopyridine and, after completion of the reaction, the organic layer was distilled under reduced pressure of 4.9 to 5.0 Torr to obtain a 90 to 93 C. fraction. Thus, there was obtained 127.9 g (yield: 85.3%) of the end product as pale yellow crystals. HPLC analysis revealed that purity of the product was 98.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With caesium carbonate; | Example 131 6-[2-(Azetidin-1-ylcarbonyl)thieno[3,2-b]pyridin-7-yl]oxy}-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide This material was prepared by reacting 2-(azetidin-1-ylcarbonyl)-7-chlorothieno(3,2-bipyridine 25a (88 mg, 0.35 mmole) with 6-hydroxy-2-methyl-1-benzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide 130a (110 mg, 0.42 mmole) and Cs2CO3 (228 mg, 0.70 mmole) in a manner similar to that previously described for example 1 to give a yellow solid (90 mg, 54%). 1H NMR (DMSO-d6, 300 MHz) delta8.58 (1H, d, J=5.46 Hz), 8.49 (1H, t, J=5.46 Hz), 7.96 (1H, d, J=2.26 Hz), 7.89 (1H, s), 7.83 (1H, d, J=8.85 Hz), 7.33 (1H, dd, J=2.35, 8.76 Hz), 6.75 (1H, d, J=5.46 Hz), 4.62 (2H, t, J=7.72 Hz), 4.10 (2H, t, J=7.82 Hz), 3.20 (2H, t, J=6.31 Hz), 2.62 (3H, s), 2.35 (2H, m), 1.07 (1H, m), 0.46 (2H, m), 0.26 (2H, m). Anal. Calcd. for C25H23N3O3S2: C, 62.87; H, 4.85; N, 8.80; S, 13.43. Found: C, 62.58; H, 4.90; N, 8.66; S, 13.33. |
Tags: 581-50-0 synthesis path| 581-50-0 SDS| 581-50-0 COA| 581-50-0 purity| 581-50-0 application| 581-50-0 NMR| 581-50-0 COA| 581-50-0 structure
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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 |
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