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CAS No. : | 26274-35-1 | MDL No. : | MFCD00972966 |
Formula : | C17H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YASXBDJBCBUIHT-UHFFFAOYSA-N |
M.W : | 231.29 | Pubchem ID : | 42014 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 75.11 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.77 cm/s |
Log Po/w (iLOGP) : | 2.73 |
Log Po/w (XLOGP3) : | 4.14 |
Log Po/w (WLOGP) : | 4.42 |
Log Po/w (MLOGP) : | 3.46 |
Log Po/w (SILICOS-IT) : | 4.59 |
Consensus Log Po/w : | 3.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.49 |
Solubility : | 0.00748 mg/ml ; 0.0000323 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.12 |
Solubility : | 0.0176 mg/ml ; 0.0000762 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.07 |
Solubility : | 0.0000199 mg/ml ; 0.0000000859 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.92 |
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 |
---|---|---|
37% | With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 30℃; for 24 h; Inert atmosphere | General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol percent), PPh3 (26 mg, 10 mol percent) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 °C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | EXAMPLE 11 2,4-Diphenylpyridine Anhydrous CeCl3 (powder, 250 mg, 1.0 mmol) was stirred in a round bottom septum glass tube at 135 C. under vacuum for 3 h. The vacuum was removed and the CeCl3 was kept under Ar and cooled in an ice bath. THF (3 mL) was added and the resulting suspension was stirred at rt overnight. Phenylmagnesium bromide (1.0 M in THF, 0.62 mL, 0.62 mmol) was added at 0 C. and the resulting suspension was stirred at 0 C. for 1.5-2 h. The mixture was cannulated into THF (3 mL) pre-swollen 2-phenyl-2,3-dihydropyridone resin (500 mg, 0.82 mmol/g, 0.41 mmol) and the resulting slurry was agitated for 3 h-overnight on a rotor. The resin was filtered, washed with 1/1 1 N AcOH (aqueous)/THF (4*4 mL), 1 N AcOH (4*2 mL), MeOH (3*2 mL), DMF (3*3 mL), THF (3*3 mL), and CH2Cl2 (3*3 mL). The resin was suspended in CH2Cl2 (5 mL) in a glass tube fitted with a gas dispensing disc, and TFA (15 mL) was added. Oxygen was bubbled through the resulting suspension for 2 days and 1:2 CH2Cl2/TFA was replenished as needed. The resin was filtered, washed with CH2Cl2 (2*2 mL) and MeOH (2*2 mL). The combined filtrates and washings were concentrated in speedvac to give the TFA salt of the product (24%). The free base was characterized: 1H NMR (300 MHz, CDCl3) delta7.47 (m, 7H), 7.70 (dd, 2H), 7.94 (s, 1H), 8.05 (dd, 2H), 8.74 (d, 1H). 13C NMR (75 MHz, CDCl3) delta118.82, 120.28, 127.04, 127.09, 128.78, 128.97, 129.05, 129.13, 138.50, 139.45, 149.31, 150.07, 158.07. LRMS (EI) m/z 231(100), 202 (21), 154(16), 127(11), 102(16), 77(19). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In methanol; ethanol; for 20h;Reflux; Inert atmosphere; | Step 3Synthesis of Compound 3A mixture of iridium trifluormethanesulfonate complex (3.0 g, 4.04 mmol), as obtained from Step 2 above, and <strong>[26274-35-1]2,4-diphenylpyridine</strong> (3.11 g, 13.45 mmol) in EtOH (30 mL) and MeOH (30 mL) was refluxed for 20 h under inert atmosphere. The reaction mixture was cooled to room temperature, diluted with ethanol, Celite was added and the mixture stirred for 10 min. The mixture was filtered on a small silica gel plug on a frit and washed with ethanol (3-4 times) and hexane (3-4 times). The filtrate was discarded. The Celite/silica plug was then washed with dichloromethane to elute the crude product. The crude product was chromatographed on silica gel with 1/1 (v/v) dichloromethane/hexane and later 4/1 (v/v) dichloromethane/hexane to yield 0.9 g of Compound 3 (28% yield), which was confirmed by HPLC (99.9% pure) and LC/MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In methanol; ethanol; for 20h;Reflux; Inert atmosphere; | Step 6Synthesis of Compound 4A mixture of iridium trifluomethanesulfonate complex (2.4 g, 3.01 mmol), obtained as in Step 5 above, and <strong>[26274-35-1]2,4-diphenylpyridine</strong> (2.4 g, 10.38 mmol) in EtOH (30 mL) and MeOH (30 mL) was refluxed for 20 h under N2 atmosphere. The reaction mixture was cooled to room temperature, diluted with ethanol, Celite was added, and the mixture was stirred for 10 min. The mixture was filtered on a small silica gel plug and washed with ethanol (3-4 times) and with hexane (3-4 times). The filtrate was discarded. The Celite/silica plug was then washed with dichloromethane to elute the product. The crude product was chromatographed on silica gel with 30% THF in hexanes to yield 1.24 g (51% yield) of Compound 4 as a yellow solid. The product was confirmed by HPLC (99.9% pure) and LC/MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | In methanol; ethanol; for 20h;Reflux; Inert atmosphere; | Step 3Synthesis of Compound 6A mixture of iridium trifluormethanesulfonate complex (2.85 g, 3.84 mmol) and 2-(dibenzo[b,d]furan-4-yl)-4,5-dimethylpyridine (2.85 g, 12.33 mmol) in EtOH (30 mL) and MeOH (30 mL) was refluxed for 20 h under inert atmosphere. The reaction mixture was cooled to room temperature, diluted with ethanol, Celite was added and the mixture stirred for 10 min. The mixture was filtered on a small silica gel plug on a frit and washed with ethanol (3-4 times) and with hexane (3-4 times). The filtrate was discarded. The Celite/silica plug was then washed with dichloromethane to elute the product. The crude product was chromatographed on silica gel with 1/1 (v/v) dichloromethane/hexane to yield 0.5 g (17% yield) of Compound 6 as a yellow solid. Compound 6 was confirmed by HPLC (99.8% pure) and LC/MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In methanol; ethanol; for 20h;Reflux; Inert atmosphere; | Synthesis of Compound 7 A mixture of iridium trifluormethanesulfonate complex (3.0 g, 3.76 mmol) and 4-(4-isobutylphenyl)-2-phenylpyridine (3.0 g, 10.44 mmol) in EtOH (30 mL) and MeOH (30 mL) was refluxed for 20 h under inert atmosphere. The reaction mixture was cooled to room temperature, diluted with ethanol, Celite was added and the mixture stirred for 10 min. The mixture was filtered on a small silica gel plug on a frit and washed with ethanol (3-4 times) and with hexane (3-4 times). The filtrate was discarded. The Celite/silica plug was then washed with dichloromethane to elute the product. The crude product was chromatographed on silica gel with toluene to yield 1.35 g (44% yield) of Compound 7 as a yellow solid. Compound 7 was confirmed by HPLC (99.9% pure) and LC/MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol; ethanol; for 20h;Reflux; Inert atmosphere; | Step 5Synthesis of Compound 8A mixture of iridium trifluoromethanesulfonate complex (3.0 g, 3.76 mmol) and 2-(dibenzo[b,d]furan-4-yl)-4,5-dimethylpyridine (3.0 g, 10.98 mmol) in EtOH (30 mL) and MeOH (30 mL) was refluxed for 20 h under inert atmosphere. The reaction mixture was cooled to room temperature, diluted with ethanol, Celite was added and the mixture stirred for 10 min. The mixture was filtered on a small silica gel plug on a frit and washed with ethanol (3-4 times) and with hexane (3-4 times). The filtrate was discarded. The Celite/silica plug was then washed with dichloromethane to elute the product. The crude product was chromatographed on silica gel with 1/1 dichloromethane/hexane to yield 2.1 g (65% yield) of Compound 8 as a yellow solid. The product was confirmed by HPLC (99.8% pure) and LC/MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With ammonium chloride; triethylamine; In acetonitrile; at 80℃; for 4h; | General procedure: The 3,5-disubstituted penta 2,4-dienal (1 mmol) andNH4Cl (1.5 mmol) were taken in a two-necked round bottomed flaskfitted with a condenser. Then 3 mL of acetonitrile and Et3N (3 mmol)were added and refluxed at 80C under air balloon for 3-4 h. After completionof the reaction, the reaction mixture was allowed to cool to room temperature,diluted with water and extracted with ethyl acetate (3 × 20 mL). The combinedorganic layer was dried over Na2SO4 and evaporated underreduced pressure. The crude product was purified by column chromatography usingsilica gel (60-120 mesh) and hexane/EtOAc as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13%; 9%; 37% | With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere; | General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9%; 65% | With 2-(diphenylphosphino)pyridine; palladium diacetate; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere; Reflux; | General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With ammonium hydroxide; copper(l) iodide; 1,10-Phenanthroline; triethylamine; In N,N-dimethyl-formamide; at 95℃; for 5h;Inert atmosphere; | General procedure: In a two necked round bottom flask a mixture of ortho-bromoaldehyde (100 mg, 0.54 mmol), phenylacetylene (66.10 mg, 0.648 mmol), aq. NH3 (2.5 M in DMF), Et3N (2 mmol), CuI (10 mol %), 9,10-Phenanthroline (0.25 mmol ) were taken in 3mL of DMF solvent in inert atmosphere. This mixture were heated to 95 oC temperature for 5 h. Completion of the reaction was confirmed by monitoring TLC. After the completion of the reaction themixture were cooled to room temperature and diluted with water and extracted with EtOAc (3×50 mL). Combined organic organic layer was washed with brine and dried over anhydrous Na2SO4. It was then evaporated under reduced pressure and desired product was isolated by column chromatography using silica gel mess and mixture of EtOAc and petroleum ether as eluents. Yellowliquid; Yields: 68 %; 1H NMR (CDCl3, 200 MHz) : 7.30-7.55(7H, m), 7.70 (2H, dd, J1= 1.4 Hz, J2 = 7.4 Hz),7.94 (1H, s), 8.10 (2H, dd, J1= 1.2 Hz, J2 = 7.6 Hz),8.74 (1H, d, J = 5.2 Hz); 13C NMR (CDCl3, 50 MHz): 119.0, 120.5, 127.3 (4C), 129.0 (2C), 129.3(2C), 129.4 (2C), 138.8, 139.7, 149.6, 150.3, 158.3; Elemental Analysis: C:88.28; H: 5.67; N: 6.06 %; Found : C: 88.24; H: 5.59; N: 6.00 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 g | In methanol; ethanol; at 65℃; for 72h; | The iridium-triflate intermediate (2.3 g, 2.96 mmol) and <strong>[26274-35-1]2,4-diphenylpyridine</strong> (2.74 g, 11.86 mmol) were mixed in 50 mL of ethanol and 50 mL of methanol. [0099] The mixture was heated to 65 degrees (oil bath temperature) for 3 days. Celite (2g) was added to the reaction and the reaction was filtered through a Celite plug. The product was washed with ethanol and hexanes. The solid was then dissolved with DCM. The solid was run through a silica gel plug to give 2 g of Compound 54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | In methanol; ethanol; at 105℃;Inert atmosphere; | To a 2L 3-neck round bottom flask was added the Iridium(III) triflate complex from the Compound 2 synthesis (above)(23.545 g, 31.5 mmol), <strong>[26274-35-1]2,4-diphenylpyridine</strong> (21.85 g, 94 mmol), 450 mL ethanol, and 450 mL methanol. The reaction mixture was heated to reflux overnight at 105 C under nitrogen. [0085] The reaction mixture was cooled to room temperature. A solid settled at the bottom and most of the dark colored liquid was decanted off. Ethanol and Celite was added and the mixture was stirred and poured on top of a silica gel plug. The plug was washed with ethanol and hexane. The product was eluted with dichloromethane. The crude was purified by columnchromatography to give 4.16 g (18%) desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With manganese(IV) oxide; oxygen; In 1,2-dichloro-ethane; at 80℃; | General procedure: After the Au(I)-catalyzed cyclization step, the dried residue wasre-dissolved in DCE (5 mL) and mixed with MnO2 (10 equiv). Oxygen gas was bubbled into themixture for 10 min, and the reaction mixture was kept stirring at 80 oC under oxygen atmospherewith an oxygen balloon. After reaction was completed, which was monitored by TLC analysis,MnO2 was removed by filtration. The filtrate was concentrated and the residue waschromatographied on a silica gel column using petroleum ether and ethyl acetate (30:1 ~ 10:1) togive pure products 3a-c. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With chloranil; acetic acid; at 118℃; | General procedure: A solution of an 1,2 addition product in AcOH (0.02 M) is treated with Chloroanil (2.0 equiv.) and refluxed for 12 h. The reaction mixture is quenched with saturated Na2CO3 solution and extracted with EtOAc. The combined extracts are dried over Na2SO4 and the solvent is removed under vacuum. The residue is purified with flash chromatography on silica gel using a mixture of hexane and ethyl acetate as an eluent to give product. |
Tags: 26274-35-1 synthesis path| 26274-35-1 SDS| 26274-35-1 COA| 26274-35-1 purity| 26274-35-1 application| 26274-35-1 NMR| 26274-35-1 COA| 26274-35-1 structure
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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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