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CAS No. : | 34486-18-5 | MDL No. : | MFCD12026108 |
Formula : | C7H6F3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VBEYJZVICNLLDA-UHFFFAOYSA-N |
M.W : | 177.12 | Pubchem ID : | 46739474 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 35.73 |
TPSA : | 22.12 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) : | -5.9 cm/s |
Log Po/w (iLOGP) : | 1.73 |
Log Po/w (XLOGP3) : | 2.08 |
Log Po/w (WLOGP) : | 3.26 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 2.34 |
Consensus Log Po/w : | 2.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.49 |
Solubility : | 0.578 mg/ml ; 0.00326 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.17 |
Solubility : | 1.19 mg/ml ; 0.0067 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.04 |
Solubility : | 0.163 mg/ml ; 0.00092 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
entspr. Halogenverb., entspr. Alkoholat; | ||
entspr. Chlorid, NaOCH3; | ||
entspr. 2-Chlorverb., Methanol; |
analog Bsp. 11; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; methyl nitrite; nitrogen(II) oxide at 24.84℃; In air; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With pyridine In dichloromethane at 20℃; for 23h; | |
In toluene at 20℃; for 2h; Glovebox; | N-Methyl-3,5-difluoro-4-methoxypyridinuim Trifluoromethanesulfonate (59). General procedure: A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with methyl trifluoromethylsulfonate (MeOTf, 51 µL, 0.46 mmol) by micropipette with polypropylene tip. The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with substrate (68 mg, 0.46 mmol) and was dissolved in PhMe (0.5 mL). The solution of pyridine was added via syringe onto the sealed vial of MeOTf at room temperature. The vial which contained the pyridine was rinsed with PhMe (0.2 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. Over the course of the reaction (2 hr), a precipitate formed. At the end of the reaction, PhMe (2 mL) was added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The residue was then rinsed with several portions of hexanes to remove any unreacted starting materials, again removing the solvent by pipette. Residual solvent was then removed in vacuo to provide the title compound (53 mg, 37%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 23 h / 20 °C 2: dimethylsulfoxide-d6 / 25 °C | ||
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 23 h / 20 °C 2: water-d2 / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.8% | With silver (II) carbonate; In dichloromethane; for 24h;Darkness; | 2-methoxy-6-ftrifluoromethyl)pyridine To a solution of <strong>[34486-06-1]6-(trifluoromethyl)pyridin-2-ol</strong> (10.0 g, 10.0 g, 61.3 mmol) in dichloromethane (3 ml/mmol, 184 ml) was added silver carbonate (22.8 g, 82.8 mmol, 3.75 mL) and iodomethane (87.0 g, 613 mmol, 38.2 mL) and stirred in the dark for 24 hours. The reaction mixture was then filtered through Celite and washed with dichloromethane. The filtrate was concentrated at 30 oC at 250 mbar, silica added and the residue was purified by chromatography eluting with 0-10percent ethyl acetate/hexane. Fractions containing product were combined to give 2-methoxy-6-(trifluoromethyl)pyridine (6.49 g, 36.6 mmol, 59.8percent yield). IHNMR (CDC13): delta 7.69 ft, J =8.1 Hz, IH) 7.25 (d, J=7.5 Hz, 1 H) 6.91 (d, J=8.6 Hz, 1 H) 3.98 (s, 3 H); |
59.8% | With silver carbonate; In dichloromethane; | 2-methoxy-6-(trifluoromethyl)pyridine To a solution of <strong>[34486-06-1]6-(trifluoromethyl)pyridin-2-ol</strong> (10.0 g, 10.0 g, 61.3 mmol) in dichloromethane (3 ml/mmol, 184 ml) was added silver carbonate (22.8 g, 82.8 mmol, 3.75 mL) and iodomethane (87.0 g, 613 mmol, 38.2 mL) and stirred in the dark for 24 hours. The reaction mixture was then filtered through Celite and washed with dichloromethane. The filtrate was concentrated at 30° C. at 250 mbar, silica added and the residue was purified by chromatography eluting with 0-10percent ethyl acetate/hexane. Fractions containing product were combined to give 2-methoxy-6-(trifluoromethyl)pyridine (6.49 g, 36.6 mmol, 59.8percent yield). 1H NMR (CDCl3): delta 7.69 (t, J=8.1 Hz, 1H) 7.25 (d, J=7.5 Hz, 1H) 6.91 (d, J=8.6 Hz, 1H) 3.98 (s, 3H); |
17% | With silver carbonate; In dichloromethane; at 20℃; for 24h;Darkness; | The suspension of 6- (trifluoromethyl) pyridin-2-ol (430 mg, 2.64 mmol) , iodomethane (3.75 g, 26.4mmol) and Ag 2CO 3 (982 mg, 3.56 mmol) in CH 2Cl 2 (8 mL) was stirred at room temperature in dark for 24 hrs. After completed, the mixture was filtered and the solvent was evaporated in vacuo at 30 . The residue was purified by column chromatography (PE/EA = 5/1) to give the product (80 mg in 17percentyield) . 1H NMR (400 MHz, CDCl 3) delta 7.76 ?7.59 (m, 1H) , 7.24 (d, J = 7.3 Hz, 1H) , 6.91 (d, J = 8.4 Hz, 1H) , 3.98 (s, 3H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 2-methoxy-6-(trifluoromethyl)pyridine With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃; for 0.75h; Stage #3: With hydrogenchloride In diethyl ether; hexane; water | 16 2-methoxy-6-f trifluoromethyl)-3-pyridyll boronic acid 2-methoxy-6-f trifluoromethyl)-3-pyridyll boronic acid To a solution of 2-methoxy-6-(trifluoromethyl)pyridine (1.0 g, 5.6 mmol) and in diethyl ether (1.2 mL/mmol, 6.8 mL) at -78 C under nitrogen was added nBuLi (2.5 mol/L) in hexanes (4.7 g, 17 mmol, 6.8 mL) over 5 min and allowed to warm up to room temperature over 30 minutes. Boric acid triisopropyl ester (2.1 g, 11 mmol, 2.6 mL) in diethyl ether (1.2 mL/mmol, 6.8 mL) was cooled to -78 C and [2-methoxy-6-(trifluoromethyl)-3-pyridyl]lithium was added to this solution over 15 minutes and then warmed up to room temperature over 30 mins. Hydrogen chloride (aqueous 25%>) (10 mL, 10 mmol) was added and the reaction mixture diluted with water and extracted twice with dichloromethane, passed through a phase separator and reduced under vacuum to give a yellow oil which solidified overnight. The reaction mixture was adsorbed onto silica and purified by chromatography on silica, eluting with 0-25% ethyl acetate/hexane. Fractions containing product were combined to give [2-methoxy-6-(trifluoromethyl)-3-pyridyl]boronic acid as a yellow solid (707 mg, 3.20 mmol, 59% yield). IHNMR (llvu941hl, CDC13): δ 8.29 (d, J=7.5 Hz, 1 H) 7.34 (d, J=7.5 Hz, 1 H) 5.92 (s, 2 H) 4.10 (s, 3 H); |
3.8 g | Stage #1: 2-methoxy-6-(trifluoromethyl)pyridine With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; | 43.3 Step 3: (2-methoxy-6- (trifluoromethyl) pyridin-3-yl) boronic acid (43-3) To the solution of 2-methoxy-6- (trifluoromethyl) pyridine (3.9 g, 22 mmol) in THF (80 mL) under nitrogen was added n-BuLi (11 mL, 26 mmol) at -78 dropwise and stirred at the same temperature for 30 mins. Then B (OiPr) 3 was added and stirred for 5 hrs while the temperature warmed to room temperature. Then 1N hydrochloride was added and stirred for 1 hr. The reaction was quenched with saturated NH 4Cl aqueous solution and the resulting mixture was extracted with ethyl acetate. The organic layers were washed with brine dried over Na 2SO 4, filtered and evaporated in vacuo to give the product (3.8 g) as yellow solid which was used directly for the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere 1.2: 0.75 h / -78 - 20 °C 2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / <i>tert</i>-butyl alcohol / 0.83 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere 1.2: 0.75 h / -78 - 20 °C 2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / <i>tert</i>-butyl alcohol / 0.83 h / 80 °C 3.1: hydrogen bromide / water / 0.75 h / 40 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere 1.2: 0.75 h / -78 - 20 °C 2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / <i>tert</i>-butyl alcohol / 0.83 h / 80 °C 3.1: hydrogen bromide / water / 0.75 h / 40 °C / Microwave irradiation 4.1: potassium carbonate / 1,2-dimethoxyethane / 0.5 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere 1.2: 0.75 h / -78 - 20 °C 2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / <i>tert</i>-butyl alcohol / 0.83 h / 80 °C 3.1: hydrogen bromide / water / 0.75 h / 40 °C / Microwave irradiation 4.1: potassium carbonate / 1,2-dimethoxyethane / 0.5 h / 75 °C 5.1: morpholine / 1.5 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether | 16 [2-methoxy-6-(trifluoromethyl)-3-pyridyl]boronic acid [2-methoxy-6-(trifluoromethyl)-3-pyridyl]boronic acid To a solution of 2-methoxy-6-(trifluoromethyl)pyridine (1.0 g, 5.6 mmol) and in diethyl ether (1.2 mL/mmol, 6.8 mL) at -78 C under nitrogen was added nBuLi (2.5 mol/L) in hexanes (4.7 g, 17 mmol, 6.8 mL) over 5 min and allowed to warm up to room temperature over 30 minutes. Boric acid triisopropyl ester (2.1 g, 11 mmol, 2.6 mL) in diethyl ether (1.2 mL/mmol, 6.8 mL) was cooled to -78 C and [2-methoxy-6-(trifluoromethyl)-3-pyridyl]lithium was added to this solution over 15 minutes and then warmed up to room temperature over 30 mins. Hydrogen chloride (aqueous 25%) (10 mL, 10 mmol) was added and the reaction mixture diluted with water and extracted twice with dichloromethane, passed through a phase separator and reduced under vacuum to give a yellow oil which solidified overnight. The reaction mixture was adsorbed onto silica and purified by chromatography on silica, eluting with 0-25% ethyl acetate/hexane. Fractions containing product were combined to give [2-methoxy-6-(trifluoromethyl)-3-pyridyl]boronic acid as a yellow solid (707 mg, 3.20 mmol, 59% yield). 1H NMR (11vu941h1, CDCl3): δ 8.29 (d, J=7.5 Hz, 1H) 7.34 (d, J=7.5 Hz, 1H) 5.92 (s, 2H) 4.10 (s, 3H); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; water / 100 °C 2: silver carbonate / dichloromethane / 24 h / 20 °C / Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane; water / 80 °C / Inert atmosphere |
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