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CAS No. : | 58861-53-3 | MDL No. : | MFCD06201382 |
Formula : | C11H8FN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MHWIDTQQBWGUCD-UHFFFAOYSA-N |
M.W : | 173.19 | Pubchem ID : | 100868 |
Synonyms : |
|
Num. heavy atoms : | 13 |
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 : | 49.63 |
TPSA : | 12.89 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) : | -5.42 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 3.31 |
Log Po/w (MLOGP) : | 2.54 |
Log Po/w (SILICOS-IT) : | 3.44 |
Consensus Log Po/w : | 2.83 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.25 |
Solubility : | 0.0972 mg/ml ; 0.000561 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.383 mg/ml ; 0.00221 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.82 |
Solubility : | 0.00265 mg/ml ; 0.0000153 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
82% | With palladium diacetate; potassium carbonate; triphenylphosphine; In methanol; acetonitrile; at 65℃; for 24h;Inert atmosphere; | General procedure: Method B: The preparation of 2-Bromopyridines with arylboronic acids was according to literature procedures.[1] To a 50-mL fire-dried flask was charged with 2-Bromopyridines (5 mmol, 1.0 eq), arylboronic acid (5.5 mmol, 1.5 eq), K2CO3 (1.38 g, 10.0 mmol, 2.0 eq), Pd(OAc)2 (56.0 mg, 0.25 mmol, 5.0 mol% ), PPh3 (131.0 mg, 0.5 mmol, 10.0 mol% ), CH3CN (10.0 mL) and methanol (5.0 mL). The mixture was degassed through a freeze-thaw-pump thread for three times. The reaction was stirred at 65 C for 24 hours. To the reaction mixture was added brine (15 mL) and ethyl acetate (15 mL). The phase was separated and the aqueous phase was extracted with ethyl acetate (4 × 15 mL). The combined organic phase was dried over Na2SO4 and concentrated under vacuum. The product was isolated by flash-column chromatography on silica gel (300-400 mesh). |
78% | With potassium phosphate; In ethanol; water; at 100℃; for 8h; | General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis. |
53% | With Pd/C; diisopropylamine; In water; at 100℃; for 24h;Green chemistry; | General procedure: An aryl halide (0.5 mmol), arylboronic acid (0.75 mmol),(i-Pr)2NH (1.0 mmol), Pd/C (1.5 mol%, 16 mg), and water (1.0mL) were allowed to react at 100 C. After a certain period, the reaction mixture was added to brine (10 mL) and extracted with ethyl acetate (3 × 10 mL). The solvent was concentrated under vacuum, and the product was isolated by short chromatography on a silica-gel (200-300 mesh) column. |
With palladium diacetate; triphenylphosphine; In ethanol; at 80℃; for 4h; | General procedure: All the 2-arylpyridines were synthesized through the couplingbetween corresponding arylboronic acids and 2-bromopyridines according toliterature procedures [1]: A mixture of Pd(OAc)2 (3 mol%),PPh3(6 mol%), arylboronic acid (7 mmol) and 2-bromopyridine (7mmol) were dissolved in ethanol (6 mL) in a 50 mL round-bottom flask and heatedto 80 oC for 4 h. Then the reaction mixture was diluted with ethylacetate (10 mL) and washed by distilled water (15 mL) for three times. Thecrude organic layers were collected and dried then the solvent was removed byevaporation. The product was obtained through column chromatographypurification with EtOAc/hexane (1/20). | |
With palladium diacetate; triphenylphosphine; In ethanol; at 80℃; for 4h; | General procedure: All the 2-arylpyridines were synthesized through the coupling between corresponding arylboronic acids and 2-bromopyridines according to literature procedures [1]: A mixture of Pd(OAc)2 (3 mol%),PPh3(6 mol%), arylboronic acid (7 mmol) and 2-bromopyridine (7 mmol) were dissolved in ethanol (6 mL) in a 50 mL round-bottom flask and heated to 80 C for 4 h. Then the reaction mixture was diluted with ethyl acetate (10 mL) and washed by distilled water (15 mL) for three times. The crude organic layers were collected and dried then the solvent was removed by evaporation. The product was obtained through column chromatography purification with EtOAc/hexane (1/20). | |
With palladium diacetate; diisopropylamine; In water; at 100℃; for 16h; | General procedure: 2-Bromopyridine (191 muL, 2 mmol), Pd(OAc)2 (10 mg, 0.02 mmol), and arylboronic acid (4 mmol) were added to a 25-mL round-bottom flask in air without any precautions. Subsequently, i-Pr2NH (1 mL)and H2O (4 mL) were added into the flask. Then a condenser was set on the round-bottom flask and the reaction was heated to reflux for16 h. The mixture was then transferred to a 100-mL separation funnel and EtOAc (20 mL) and H2O (20 mL) were added. The organic layer were collected and the solvent was removed used a rota-vapor. The crude product was purified by column chromatography. | |
With palladium diacetate; potassium carbonate; In ethanol; water; at 80℃; | General procedure: A mixture of 2-bromopyridine derivatives (1 mmol),1.5 equiv. of arylboronic acid, 2 equiv. of K2CO3, Pd(OAc)2 (1.5 mol%), ethanol/water (3:1 v/v) was stirred at 80 C in air for the indicated time. The reaction mixture was added to brine (20 mL) and extracted with dichloromethane. The solvent was concentrated under vacuum, and the product was isolated by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With iodine; palladium diacetate; In 1,2-dichloro-ethane; at 110℃; for 24h; | General procedure: To a 5-mL V-shape tube were added Pd(OAc)2 (2.5 mg, 0.01 mmol), I2(40 mg, 0.16 mmol), 2-phenylpyridine (30 muL, 0.2 mmol), and DCE (0.5 mL). Then the tube was heated in a pre-heated 110 C oil bath for 24 h. Subsequently, the volatiles were removed by rota-vapor and the residue was purified by column chromatography (30% EtOAc in hexane) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane;Inert atmosphere; Reflux; | General procedure: To a two necked, 100 mL round bottom flask equipped with a magnetic stir bar were added 2-chloropyridine (1 equiv), phenylboronic acid (1.2 equiv), triphenylphosphine (0.1 equiv), 2 M potassium carbonate (2.7 equiv) and ethylene glycol dimethyl ether(0.9 M). The mixture was degased with Ar for 15 min. Then Pd(OAc)2 (2.5 mol%) was added to the reaction mixture and degassing continued for 15 more minutes and then the outlet was removed. The reaction mixture was heated to reflux. The progress of reaction was monitored by TLC (hexane:EtOAc 90:10). Upon completion (typically 18-24 h), reaction mixture was cooled to room temperature and then extracted with DCM (3x20 mL). The combined organic portion was washed with water (3x20 mL) and brine (1 20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. The crude material was purified by flash chromatography to obtain pure ligand. |
49% | With potassium phosphate; In ethanol; water; at 100℃; for 8h; | General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tert.-butylhydroperoxide; palladium diacetate In tetrahydrofuran at 100℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With oxone; Ru(MesCO2)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at 140℃;Sealed tube; Green chemistry; | General procedure: A mixture of 2-arylpyridines (1 eq), Ru(MesCO2)(L) (p-cymene) [L- 2,2?-bypyridine or 4,4?-dibromobipyridine] (5 mol%), TFA: TFAA=0.6 ml:0.4 ml and Oxone (4 eq) was taken in a 30 ml sealed tube. 1 ml of DCE was added and the tube was then placed in an oil bath, stirred, and heated at 140C. The progress of the reaction was checked after every 8 hrs. After complete consumption of starting material the reaction mixture was cooled to room temperature, quenched with brine and extracted with dichloromethane. The combined organic layer was dried with anhydrous Na2SO4, and vacuum evaporated. The crude product was purified over a column of silica gel (eluent: hexane/ethyl acetate) to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tert.-butylhydroperoxide; In water; chlorobenzene; at 120℃; for 8h; | General procedure: In a typical reaction, a 10 mL oven-dried reaction vessel was charged with Pd/MgLa mixed oxide (30 mg), 2-phenylpyridine (29 mg, 0.2 mmol), benzyl alcohol (108 mg, 1 mmol), tert-butyl hydroperoxide (70% solution in water, ?129 mg, 1 mmol) and chlorobenzene (0.5 mL) were added. The resulting solution was stirred at 120 C for 8 h in open air. The reaction was monitored by thin-layer chromatography (TLC). After cooling to room temperature, catalyst was separated by simple centrifugation. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography using silica gel and a mixture of hexane/ethyl acetate as eluents. All the products were confirmed by 1H NMR and 13C NMR spectroscopy. The recovered catalyst was used for the next cycle without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 15 h / 20 °C / Inert atmosphere 2: dichloro(1,3-bis(dicyclohexylphosphino)propane)palladium; copper(l) iodide; (2-hydroxyethyl)(methyl)amine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylsilane; 1,10-Phenanthroline; nickel(II) chloride hexahydrate; zinc; In N,N-dimethyl-formamide; at 100℃; for 8h;Inert atmosphere; | To the reaction tube were added 5 mg of NiCl2.6H2O (5 mol%), Phen 4 mg (5 mol%), zinc powder 2.6 mg (10 mol%),After nitrogen replacement three times, 2 ml DMF was injected,66 mul (0.4 mmol) of 2- (2,4-difluorophenyl) pyridine and 96 mul of Et3SiH (0.6 mmol, 1.5 equiv) were added and heated at 100 C. for 8 h.60ml ethyl acetate, 20ml washed three times, 20ml saturated brine, dried over anhydrous Na2SO4,The organic solution was concentrated under reduced pressure and finally purified by silica gel column (petroleum ether: ethyl acetate = 100: 1). Yield: 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C26H36N3(1+)*BF4(1-); potassium tert-butylate; In hexane; at 25℃; for 24h;Inert atmosphere; Glovebox; | General procedure: In a nitrogen-filled glovebox, to an oven-dried 25-mL Schlenk tube was charged with [Rh(COD)Cl]2 (2.5mg, 2.5mol%), L6 (4.8mg, 5.0mol%) and KOtBu (1.1mg, 5.0mol%) and n-hexane (1.0mL). The reaction mixture was allowed to stir for 2h at room temperature, followed by adding 1a (0.2mmol) and B2pin2 (50.8mg, 0.2mmol, 1.0 equiv). The reaction was then stirred for the determined time at 25C. The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography (petroleum ether/ethyl acetate/triethylamine 4:1:1% to ethyl acetate/triethylamine 1:1%) on neutral Al2O3 (300-400 mesh). The reactions were repeated two runs. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide; In tetrahydrofuran; at 20℃; for 24h;Schlenk technique; | General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In water; at 200℃; under 1551.49 Torr;Inert atmosphere; | General procedure: A Parr reactor (1 L model 4533, Fig. S1) was charged withiridium (III) chloride (1 equiv), ligand (12 equiv), sodium carbonate(6 equiv) and DI water (0.03 M). The reaction mixture was pressurized(30 PSI) and depressurized with Ar (3) and finally charged again with Ar before sealing. The reaction mixture was heated at 200 C for 24-48 h. After cooling to room temperature, reaction mixture was extracted with DCM (3 20 mL). The combined organic portion was filtered through celite pad which was then concentrated to obtain crude product. The pure compound 3a-3f was obtained by performing flash chromatography. For most complexes, (3a-3d) crude samples were dry loaded on silica prior to running the column due to low solubility of the complex. After elution of the ligand with hexane/ethyl acetate the eluting solvent was switched to dichloromethane, which facilitated the elution ofthe iridium complexes (3a-3f). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) sulfate; glycine; at 140℃; for 24h;Inert atmosphere; | General procedure: In an argon-filled screwed text tube, 2-phenylpyridines (0.5 mmol), anhydrous copper sulfate (79.9 mg, 0.5 mmol), glycine (3.8 mg, 0.05 mmol), and dimethyl sulfoxide (0.1 mL, 1.4 mmol) were added. The reaction mixture was stirred at 140 C in a preheated oil bath for 24 h. The temperature was lowered to room temperature, and water (10 mL) was added. The reaction mixture was extracted with ethyl acetate (10 mL x 3), and the organic layer was collected, washed with brine, dried with anhydrous Na2SO4 and concentrated by a rotary evaporator. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 120℃; for 24h;Inert atmosphere; | General procedure: Under N2 atmosphere, an oven-dried reaction vessel was charged with 2-arylpyridine 1 (0.3mmol), N-(arylthio)benzamide 2 (0.45mmol for monothiolation and 1.2mmol for dithiolation), Pd(MeCN)2Cl2 (0.03mmol) and dry DMF (2mL). The vessel was sealed and heated at 120C (oil bath temperature) for 24h and then cooled to room temperature. Brine and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate three times, and the combined organic layer was dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica-gel column chromatography to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 120℃; for 24h;Inert atmosphere; | General procedure: Under N2 atmosphere, an oven-dried reaction vessel was charged with 2-arylpyridine 1 (0.3mmol), N-(arylthio)benzamide 2 (0.45mmol for monothiolation and 1.2mmol for dithiolation), Pd(MeCN)2Cl2 (0.03mmol) and dry DMF (2mL). The vessel was sealed and heated at 120C (oil bath temperature) for 24h and then cooled to room temperature. Brine and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate three times, and the combined organic layer was dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica-gel column chromatography to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With dipotassium peroxodisulfate; water; copper diacetate; palladium diacetate; In dimethyl sulfoxide; at 120℃; for 24h;Inert atmosphere; | General procedure: A mixture of 1 (0.5 mmol), 2 (0.6 mmol), DMSO (5% H2O aq, 5mL), Pd(OAc)2 (5 mol%), Cu(OAc)2 (10 mol%), and K2S2O8 (2equiv) was stirred at 120 C under Ar atmosphere for 24 h. Thereaction mixture was washed with H2O, and the aqueous phasewas extracted with EtOAc (3×). The combined organic layer waswashed with brine, dried over Na2SO4, and evaporated underreduced pressure. The crude product was purified by silica gelcolumn chromatography to give the corresponding products(3a-d,7b 3f-k,7b 3n-s7b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With palladium diacetate; In 1,2-dichloro-ethane; toluene; at 85℃; for 8h;Inert atmosphere; Sealed tube; | General procedure: A mixture of 2-arylpyridine (0.3 mmol), iodobenzenedibenzoates (0.315 mmol) and Pd(OAc)2(5 mol%) were added into a vial containing a stirring bar and sealed witha Teflon-lined cap. The vial was evacuated and refilled with nitrogen, thenDCE/toluene (4:1, 2 mL) was introduced. The resulting mixture was stirred at 85oC for 8 h. After the reaction was complete, the mixture was addedinto H2O (25 mL) and extracted with ethyl acetate (10 mL) for threetimes. The combined organic layer was dried over anhydrous Na2SO4and filtered. After removal of the solvent in vacuo, the residue was purifiedby column chromatography (EtOAc /hexane)to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bromopentacarbonylmanganese(I); at 50℃; for 4h;Ionic liquid; | General procedure: Starting material 1 (0.2 mmol), dioxazolones 2 (0.21 mmol), MnBr(CO)5 (2.5 mol %) and [Hmim]OAc (1 mL) were added to an oven-dried 25 mL-vial equipped with a stir bar, The reaction mixture was stirred in a pre-heated oil bath at 50 oC for 4 h in an oil bath with vigorous stirring. Upon completion, the mixture was diluted with H2O. The layer was separated, and the aqueous layer was extracted with ethyl acetate (10 mL 3). The combined organic layers were dried over MgSO4. The solvents were removed under reduced pressure, and the crude reaction mixture was purified by chromatography on silica gel (n-hexanes/EtOAc) as an eluent to give the desired product 3. Reuse of MnBr(CO)5/[Hmim]OAc catalytic system. The reaction was set up the same as above. After the reaction was complete, diethyl ether (20 mL) was added to extract the product 3 from the reaction mixture, the ionic liquid containing the Mn catalyst was separated and could be used for next reaction without further treatment. After removal of excess ether solvent, the product 3 was purified by chromatography on silica gel (n-hexanes/EtOAc) as an eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tert.-butylhydroperoxide; palladium dichloride; XPhos; In chlorobenzene; at 130℃; for 8h; | General procedure: To a mixture of 2-arylpyridines (0.3 mmol) in chlorobenzene (2 mL), styrenes, phenylacetylenes or styrene epoxide (0.9 or 1.8 mmol), PdCl2 (5mol%) and TBHP (2.7 or 3.6 mmol) were added. The resulting mixture was heatedat 130 C temperature for 8 h. After the reaction was complete, the mixture was added into H2O (25 mL) and extracted with ethyl acetate (10 mL) for three times. The combined organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent in vacuo, the residue was purified by column chromatography (ethyl acetate/hexane) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In acetic acid; at 20℃; for 12h;Schlenk technique; Inert atmosphere; | General procedure: To a dried Schlenk tube was equipped with a magnetic stirbar. [Cp*RhCl2]2 (0.005 mmol, 2.5 mol %, 3.1 mg), AgSbF6 (0.03 mmol, 15 mol %,10.3 mg), substrate 1 (0.2 mmol or 0.4 mmol), HOAc (1 ml), substrate 2 (0.24 mmolor 0.2 mmol) were added sequentially under argon. The tube was stirred at roomtemperature or 80 C for 12 h. After completion of the reaction, the mixture wasdiluted with EtOAc (10 mL), filtered through a short pad of silica gel and washedwith EtOAc (30 mL). The filtrate was pre-absorbed on silica gel and concentrated byrotary evaporation. The crude product was purified by flash silica gel (300-400 mesh)chromatography to afford the desired products product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dichloro bis(acetonitrile) palladium(II); In water; dimethyl sulfoxide; at 100℃; for 24h;Sealed tube; | General procedure: A mixture of arenes 1 (0.10mmol), N-PSP 2a (71mg, 0.20mmol), PdCl2(CH3CN)2 (3mg, 0.01mmol) and DMSO/H2O mixed solvents (v/v=1:1, 1.0mL) was added to a 25mL sealed tube under air atmosphere, then stirred at 100C for 24h. After cooling to ambient temperature, the resulting mixture was extracted with EtOAc (3×10mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and all the volatiles were evaporated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleum ether (35-60C)/Et2O=30:1, v/v) to afford the desired products 3 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With dichloro bis(acetonitrile) palladium(II); In water; dimethyl sulfoxide; at 100℃; for 24h;Sealed tube; | General procedure: A mixture of arenes 1 (0.10mmol), N-PSP 2a (71mg, 0.20mmol), PdCl2(CH3CN)2 (3mg, 0.01mmol) and DMSO/H2O mixed solvents (v/v=4:1, 1.0mL) was added to a 25mL sealed tube under air atmosphere, then stirred at 100C for 24h. After cooling to ambient temperature, the resulting mixture was extracted with EtOAc (3×10mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and all the volatiles were evaporated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleum ether (35-60C)/Et2O=30:1, v/v) to afford the desired products 4 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With oxygen; In methanol; at 120℃; under 760.051 Torr; for 22h; | The 2 - (4 - fluorophenyl) - pyridine 1g (86.6 mg, 0.5 mmol), 1, 2 - diphenyl acetylene 2a (89.7 mg, 0.5 mmol), Cp * Rh (H2 O)3 (OTf)2 (3.0 mg, 1 mol %), HOTf (44 muL, 0.5 mmol), adding 2.0 ml in methanol, oxygen (1atm), 120 o C reaction 22 hours after stopping the reaction, diatomaceous earth filter, dichloromethane washing, to collect organic phase of the drying solvent, methanol/ethyl ether/petroleum ether (1:4: 100) washing, to get the pure product isoquinoline salt derivative 3ga. The product is a white solid, yield 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen; triethylamine In methanol; water at 120℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bromopentacarbonylmanganese(I); In dichloromethane; at 80℃; for 12h;Schlenk technique; | 2- (p-fluorophenyl) pyridine (59.4 mg, 0.3 mmol), N-cyano-N-p-methoxyphenyl-p-benzenesulfonamide (90.6 mg, 0.3 mmol)And manganese pentacarbonyl (0.9 mg, 0.003 mmol)And sequentially added to a 25 mL Schlenk reaction flask,Then, dichloromethane (5.9 mL) was added,And placed in 80 oil bath reaction 12h. After completion of the reaction, the solvent was removed under reduced pressure , Using petroleum ether / ethyl acetate as eluent, silica gel column separation,The yield was 89%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With [2,2]bipyridinyl; copper(l) iodide; In 1-methyl-pyrrolidin-2-one; benzene; at 65℃; for 8h;Inert atmosphere; Schlenk technique; | Under a nitrogen atmosphere, 15 mL of a clean, clean Schlenk tube was charged with 2-pyridine fluorosulfonate (354.3 mg, 2.0 mmol), CuI (3.8 mg, 0.02 mmol), bipyridyl(6.4 mg, 0.04 mmol) (1.6 mL) N-methyl pyrrolidone (3.0 ml) and 4-fluorophenylzinc chloride in benzene (7.1 mL, 0.35 mol / L, 2.5 mmol). The Schlenk tube was then heated in a 65 C oil bath for 8 hours, at which point TLC showed complete reaction of the starting material. The Schlenk tube was then cooled in an ice-water bath and 2.O mL of purified water was added to the reaction system to carry out the quenching reaction. After stirring at room temperature for 15 minutes, the layers were allowed to stand to obtain an aqueous phase and an organic phase. The aqueous phase was extracted with dichloromethane (3 mL X3) and the extracted extract was combined with the above organic phases and dried over anhydrous sodium sulfate. Filtration to obtain a filtrate. The filtrate was concentrated and chromatographed on silica gel to give the product as a pale yellow product 249 mg, yield 72%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver sulfate; In 1,2-dichloro-ethane; at 80℃; for 12h;Sealed tube; | Add 0.3 mmol of p-fluoro-2-phenylpyridine to a dry 15 ml sealed tube.And methylene diphosphonic acid tetraethyl 0.36mmol,Catalyst dichloro(pentamethylcyclopentadienyl) ruthenium (III) dimer (CAS No. 12354-85-7) 5% mol,Silver sulfate 10% mol and solvent DCE 3 ml were stirred at 80 C for 12 hours.After completion of the reaction, concentration under reduced pressure, column chromatography, DCM/MeOH (80:1)Obtaining a yellow oil product, 99.2 mg, yield 72%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In water at 205℃; for 48h; Inert atmosphere; | 6 Example 6 - Synthesis of (0169) fac-Trisf5-fluoro-2-(2-pyridinyl-N)phenyl-Cliridium(lll)) Photocatalyst (FIG.21) (0170) [0156] Iridium (III) chloride anhydrous (0.47 g, 1.36 mmol, 1 equivalent), 2-(4- fluorophenyl)-pyridine (2.83 g, 16.4 mmol, 12.0 equivalents), and 0.41 L of Dl water (0.003 M with respect to IrCU) were added to a 1 L Parr reactor. The reaction mixture was pressurized with argon (10.0 psi), stirred, and then depressurized three times, and finally charged again with argon before sealing. The reaction mixture was heated to 205°C for 48 h. Then the reactor was cooled, and the reactor was opened after cooling, revealing an insoluble yellow solid on the surfaces and dispersed in the aqueous phase. All contents were transferred slowly to a 4 L separatory funnel aided by a large 5 cm glass funnel. Then the interior of the reactor was mechanically scraped (to extract the yellow material) with metal tongs, cotton balls, and 250 mL of dichloromethane (DCM) from a spray bottle, and again all contents were added to the separatory funnel. [0157] While still in the funnel, the cotton was rinsed with 25 mL of DCM from a spray bottle and evenly pressed with tongs to release the yellow material from the cotton. After removing the cotton, the solution was then diluted with 1.0 L of DCM. The separatory funnel was shaken vigorously, allowed to settle and again shaken, and the organic layer was then slowly separated from the aqueous layer; the aqueous layer was further extracted with more DCM (3 x 10 mL), and the organic layers were combined. The aqueous layers were kept for future ligand recovery. The combined organic layer was washed with a 1 M HCI solution, with vigorous mixing prior to separation (3 x 500 mL). Each HCI wash was then back extracted with DCM (3 x 10 mL) to insure complete recovery of the product. After the final wash, the organic layer was filtered slowly (20 min) through a CELITE (25 g) pad (Imerys Minerals California, Inc., San Jose, CA) on top of a 150 mL medium porosity sintered glass funnel, into a 3 L round- bottomed flask, and then dried with 30 g of MgSCu. After filtering the drying reagent using a 4 L Erienmeyer flask fitted with a 5 cm funnel/cotton plug, a homogenous aliquot was removed for NM analysis. Finally, the solvent was removed in batches by transferring to a 2.5 L round- bottomed flask by rotary evaporation (35°C, 30 mm Hg, 150 rpm) to afford 963 mg (96%) of lr(Fppy)3 as a bright yellow solid. (0171) [0158] FIG. 22 -- *H NM R(Methylene Chloride-d2, 400 MHz): d δ 7.88 (d, 3H, J = 8.2 Hz), 7.72-7.64 (m, 6H), 7.52 (ddd, 3H, J = 5.5, 1.6, 0.8 Hz), 6.94 (ddd, 3H, J = 7.1, 5.6, 1.3 Hz), 6.63 (td, 3H, J = 8.7, 2.7 Hz), 6.39 (dd, 3H, J = 10.3, 2.7 Hz) ppm. 13C NMR(Methylene Chloride-d2, 101 MHz): d δ 165.3 (d, J = 5.4 Hz), 163.4 (d, J = 5.7 Hz), 162.8, 147.2, 140.2, 136.6, 125.8 (d, J = 9.2 Hz), 122.0, 121.8 (d, J = 16.4 Hz), 118.9, 107.4 (d, J = 23.6 Hz) ppm. (0172) [0159] FIG. 23 -- 19F NMR (376 MHz, Methylene Chloride d2) d 112.33 (ddd, J = 10.3, 9.1, 5.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tert.-butylhydroperoxide; copper(l) iodide; 1,2-dichloro-ethane; at 90℃; for 24h;Sealed tube; | General procedure: A sealed tube, equipped with a stir bar was charged with 2-phenylpyridine (1.0 equiv), TBHP (5.0 equiv), CuI (20 mol %) and 1,2-Dichloroethane (2.0 mL) was added, and the vial was closed with a screw tightly. The resulting mixture was heated in an oil bath at 90 C for 24 h, cooled, and the mixture was extracted with EtOAc. The extract was washed with brine (2 x 15mL) and dried over Na2SO4. After evaporation, the residue was purified via column chromatography (hexanes-EtOAc) to give the corresponding product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With [RhCl2(p-cymene)]2; oxygen; copper diacetate; In 1-methyl-pyrrolidin-2-one; at 105 - 110℃; for 24h;Enzymatic reaction; | The corresponding compound of formula II (173 mg, 1 mmol) (2 - chloro phenylpyridyl), pyrrole (670 mg, 10 mmol), N - methyl pyrrolidone (40 ml), [RuCl2(P - cymene)]2(15 Mg, 0 . 025 mmol) and a hydrated copper acetate (500 mg, 2.5 mmol) put into the clean reaction vessel, the oxygen gas in the container for replacement three times after pressure-fluorine bottle plug is sealed, then heated to 105 C -110 C, in the presence of oxygen, heat insulation on the oxidative dehydrogenation coupling reaction 24 hours, after the reaction, the reaction liquid slow cooling to room temperature, the synthetic liquid filtering, and 10 ml N - methyl pyrrolidone leaching, the combined filtrate is concentrated under reduced pressure to remove the solvent, the residue by silica gel column chromatography (eluant: hexane (volume)/ethyl acetate (volume) ratio of 2:1) for refining, concentrated or after crystallization, to obtain the corresponding shallow pink solid product biaryl pyrrole derivative compounds Id (129 mg), yield 54%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With P(t-Bu)3 Palladacycle Gen. 3; potassium trimethylsilonate In tetrahydrofuran at 23℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium diacetate; potassium carbonate; tricyclohexylphosphine In 1,4-dioxane at 150℃; for 16h; Inert atmosphere; Sealed tube; Microwave irradiation; |
Tags: 58861-53-3 synthesis path| 58861-53-3 SDS| 58861-53-3 COA| 58861-53-3 purity| 58861-53-3 application| 58861-53-3 NMR| 58861-53-3 COA| 58861-53-3 structure
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