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CAS No. : | 177202-83-4 | MDL No. : | MFCD08060516 |
Formula : | C11H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MTYHJHATMPCNLW-UHFFFAOYSA-N |
M.W : | 170.21 | Pubchem ID : | 459519 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With sulfuric acid; orthoarsenic acid at 170℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 2-(pyridin-3-yl)phenylamine With acetic acid; sodium nitrite In water at 0℃; for 1.5h; Inert atmosphere; Stage #2: With sodium azide In water at 0 - 20℃; Inert atmosphere; | |
90% | Stage #1: 2-(pyridin-3-yl)phenylamine With acetic acid; sodium nitrite In water at 0℃; for 1.5h; Inert atmosphere; Stage #2: With sodium azide In water at 20℃; for 0.5h; Inert atmosphere; | |
With hydrogenchloride; sodium azide; sodium nitrite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.6% | With hydrogen In methanol for 3.5h; | 7.2 Step 2; 2-PYRIDIN-3-VL-PHENYLAMINE A solution of the title compound from the previous step (16.3 g, 81 MMOL) in methanol (300 ml) was hydrogenated (50 psi; 1.65 g of platinum oxide catalyst) for 3.5 hours. The catalyst was filtered, and the filtrate was concentrated IN VACUO to afford a viscous amber oil. Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with ethyl acetate) afforded the title compound 13.5 g, (94.6% yield) as an amber oil. MS m/z 171 (M+ 1). 1H NMR (400 MHz, CDCI3) δ 8.71 (1H, m), 8.58 (1H, m), 7.80 (1H, m), 7.37 (1H, m), 7.19 (1H, m), 7.10 (1H, m), 6.84 (1H, m), 6.78 (1H, m), 3.70 (2H, broad s) ppm. |
With hydrogenchloride; tin(ll) chloride | ||
With hydrogenchloride; tin(ll) chloride |
With palladium 10% on activated carbon; ammonium formate In methanol for 0.666667h; Inert atmosphere; | ||
With iron; ammonium chloride In water; isopropyl alcohol Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65 mg | With barium dihydroxide In 1,4-dioxane at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 18% 2: 4% 3: 4% | With 2,2'-azobis(isobutyronitrile); diphenyl diselenide; tri-n-butyl-tin hydride at 95℃; for 17h; | |
1: 18% 2: 4% 3: 4% | With 2,2'-azobis(isobutyronitrile); diphenyl diselenide; tri-n-butyl-tin hydride for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 2-(pyridin-3-yl)phenylamine With bromocyane In ethanol at 40℃; for 0.333333h; Stage #2: With water; ammonium chloride In ethanol at 40℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium carbonate In 1,4-dioxane; water for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N; [1,1'-biphenyl]-2-yldicyclohexylphosphine / Pd(OAc)2 / dioxane / 1 h / 80 °C 2: 65 mg / aq. Ba(OH)2 / dioxane / 4 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine 2: aqueous HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid; sodium nitrite; sodium azide 2: decalin / 180 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.1% | With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 100 - 140℃; for 3h; Heating / reflux; | 8.1 EXAMPLE 8; ENANTIOMERIC (BOTH ENANTIOMERS) AND RACEMIC 3-METHYL-8-PIPERIDIN-3-YL- QUINOLINE; Step 1; 3-METHYL-8-PYRIDIN-3-YL-QUINOLINE A well-stirred mixture consisting of Example 7, Step 2 (3.20 g, 18.8 MMOL), 2.51 g (11.1 mmol) of sodium -nitrobenzene sulfonate, 5.1 g (51.9 MMOL) of concentrated sulfuric acid, and water (1.89 ML) was heated to 100°C. 2-Methyl acrolein (1.0 MI, 12.1 MMOL) was added, and the reaction temperature was maintained at 100°C for 1 hour. The reaction temperature was then elevated to 110°C, an additional 1 ml (12.1 MMOL) portion of 2-methyl acrolein was added, and the 110°C reaction temperature was maintained for 1 hour. Subsequently, the above described sequence of elevating the reaction temperature by 10°C increments, followed by an addition of 1.0 mi of 2-methyl acrolein and an hour of heating at the newly established temperature was repeated three more times (with reaction temperatures of 120°C, 130°C, and finally, 140°C). The reaction temperature was then lowered to and maintained at 90°C, affording an acidic aqueous phase and a pliable tacky gum. The acidic layer was carefully siphoned off, and the residual gum was thoroughly triturated/pulped with several 25 ml portions of 1 N hydrochloric acid. The combined acidic aqueous extracts were made basic (pH = 14) by addition of 50% aqueous sodium hydroxide and, in turn, extracted with two 50 ml portions of methylene chloride. The organic extract was dried (anhydrous sodium sulfate) and concentrated in vacuo to afford an amber syrup. Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with ethyl acetate) yielded the title compound (790 mg, 19. 1% YIELD) as a viscous colorless syrup. MSM/Z221 (M+1). 1 H NMR (400 MHz, CDCI3) δ 8. 91 (1H, m), 8.77 (1H, m), 8.63 (1H, m), 8.07 (1H, m), 7.97 (1 H. m), 7.66 (1 H, m), 7.60 (1 H, m), 7.40 (1 H, m), 2.52 (3H, s) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With lithium triethylborohydride In tetrahydrofuran at 20 - 25℃; for 18h; | 7.3 STEP 3; Racemic-2-Piperidin-3-yl-phenylamine To a well-stirred solution of the title compound from the previous step (1.83 g, 10.8 MMOL) in tetrahydrofuran (5.0 ML), 37.8 ml (37.8 MMOL) of 1M lithium triethylborohydride in tetrahydrofuran was added dropwise over a 15 minute period. The reaction mixture was then stirred at ambient temperature for 18 hours. The reaction was then quenched by cautious dropwise addition of water (100 ML). Solvents were removed in vacuo, yielding a viscous oil. Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with methylene chloride/methanol/concentrated aqueous ammonium hydroxide =90 : 9: 1 in volume) afforded (after appropriate combining of chromatography column fractions of similar purity as per thin layer chromatography inspection) a 470 mg viscous syrup sample (which solidified on standing, shown to be predominantly title compound product by NMR inspection) and a considerably less pure sample of the desire product (600 mg, a viscous OIL). Trituration of the 470 mg sample with methylene chloride (2 ML) afforded a 100 mg sample of the title compound (a colorless amorphous solid, isolated by suction filtration; no detectable impurities by NMR inspection). A second flash chromatography of the entire aforedescribed 600 mg impure sample (same chromatography conditions) yielded an additional 160 mg of the purified title compound product (colorless amorphous solid; 260 mg, 14% yield). MSm/z177 (M+1). 'H NMR (400 MHz, CDCI3) δ 9.40 (1H, m), 9.33 (1H, m), 9.10 (1H, m), 9.05 (1H, M), 5.60 (2H. m), 5.0-5. 34 (3H, overlapping multiplets), 4.30 (2H, m), 4.12 (2H, m) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 3.1: ruthenium trichloride hydrate / Isopropyl acetate / 15 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 3.1: ruthenium trichloride hydrate / Isopropyl acetate / 15 h / 80 °C / Inert atmosphere 4.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Inert atmosphere; | |
99% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Inert atmosphere; | |
75% | With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; palladium dichloride In 1,4-dioxane; water at 80℃; for 5h; Inert atmosphere; |
72% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water at 20 - 100℃; for 1.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 4.1.3. General procedure for 14a-m General procedure: To a solution of corresponding aniline/benzyl amine (1.0 mmol) in 10 mL dioxane:water (1:1), was added anhydrous K2CO3 (1.5 mmol), aryl boronic acids (1.2 mmol) and Pd(TPP)2Cl2 (0.025 mmol) in a seal tube. The mixture was purged with argon for 30 min at rt and heated at 100 °C for 1 h in microwave. All reactions and manipulations were run under argon atmosphere. After completion, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on a silica gel to give the desired product. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 3.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere; Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 3.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere; Molecular sieve 4.1: sodium carbonate / chloroform; water / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | General Procedure for the Stille Cross-Coupling of 2a with Alkenyl or Aryl Halides 12. General procedure: A mixture of 2a (60 mg, 0.16 mmol, 1.1 equiv) and the halide 12 (see Table 2; 0.14 mmol, 1 equiv) in dry DMF (1.4 mL) was purged with Ar for 10 min. To this solution was added either Pd2(dba)3•CHCl3 (10 mg, 0.014 mmol, 0.1 equiv) and AsPh3 (12 mg, 0.06 mmol, 0.4 equiv) simultaneously (entries 2-4 in Table 2), or first CsF (40 mg, 0.28 mmol, 2 equiv) then Pd(PPh3)4 (8 mg, 0.014 mmol, 0.1 equiv) and CuI (4 mg, 0.03 mmol, 0.2 equiv, entries 1, 5-8). The mixture was purged with Ar for an additional 10 min and stirred at rt for 16 h. The resulting mixture was diluted with brine (1 mL) and EtOAc (10 mL), and the organic phase was washed with a 1:1 mixture of water and brine (3 mL x 3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give crude coupling products 13a-f. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether; pentane / 3.5 h / -40 - 0 °C / Inert atmosphere 1.2: 6 h / -78 - 0 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With copper(l) iodide; C37H51ClFeNPPd; cesium fluoride; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; | General procedure: 4.Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.3.7 3-(2-Aminophenyl)pyridine (3ga) 15 Oil liquid; 1H NMR (400 MHz, CDCl3): delta=8.69 (s, 1H), 8.56 (d, J=2.68 Hz, 1H), 7.78 (d, J=7.52 Hz, 1H), 7.34 (t, J=6.56 Hz, 1H), 7.17 (t, J=7.36 Hz, 1H), 7.07 (d, J=7.20 Hz, 1H), 6.83 (t, J=7.24 Hz, 1H), 6.76 (d, J=7.84 Hz, 1H), 3.72 (s, 2H); 13C NMR (100 MHz, CDCl3): delta=115.9, 118.9, 123.6, 129.4, 130.6, 135.3, 136.6, 143.8, 148.4, 150.1; HRMS-ESI (m/z): [M+H]+ calcd for C11H11N2+: 171.0917, found: 171.0918. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether / 2 h / -78 °C 1.2: 3 h / -78 °C 2.1: C37H51ClFeNPPd; copper(l) iodide; cesium fluoride / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In tetrahydrofuran at 20℃; | 4.1.7. General procedure for 20a-n General procedure: Phthalisoimide 19a-b (1 equiv)was added to stirring solution ofthe aniline/benzylamine 14a-m (1.2 equiv) in THF. The mixture was stirred overnight at room temperature. The THF was evaporated on a rotavapor. The mixture was diluted with EtOAc (triple thevolume of THF) and washed three times with 1 M HCl. The organic phase was dried with Na2SO4 and evaporated. The product was purified by flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bromocyane / ethanol / 1 h / Reflux 2.1: potassium hydroxide; potassium carbonate / N,N-dimethyl-formamide / 20 °C / Microwave irradiation 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: bromocyane / ethanol / 1 h / Reflux 2.1: potassium hydroxide; potassium carbonate / N,N-dimethyl-formamide / 20 °C / Microwave irradiation 2.2: 2 h / 20 °C 3.1: 1H-tetrazole / acetonitrile / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(pyridin-3-yl)phenylamine With bromocyane In ethanol for 1h; Reflux; Stage #2: With water; ammonium chloride In ethanol | IV Synthesis of 3-(1H-indol-3-yDacrylaldehyde Synthesis of 3-(1H-indol-3-yDacrylaldehyde Reference: Aaron M. Kearney, Christopher D. Vanderwal Angew. Chem. Int. Ed. 2006, 45, 7803-7806. To a solution of 10.0 g of 2-(pyridin-3-yl)aniline (58.7 mmol) in 100 mL ethanol is slowly added 6.2 mL of cyanogen bromide (12.4 g, 118 mmol). The reaction is heated to reflux for 1 hour, monitoring by TLC (silica, hexanes:ethyl acetate 1:1) for formation of the Zincke salt. The reaction is then quenched via addition of 50 mL saturated NH4Cl, and extracted with 3*50 mL dichloromethane. The combined organic layers are washed 3*100 mL saturated NH4Cl, followed by drying over anhydrous Na2SO4 and removal of the solvent. The crude residue is further purified via column chromatography over silica, using a hexanes-ethyl acetate gradient. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
507 mg | Stage #1: 2-(pyridin-3-yl)phenylamine With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With potassium iodide In water at 20℃; for 0.666667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 0.67 h / 20 °C / Inert atmosphere 2.1: benzene / 24 h / 20 °C / Inert atmosphere; Glovebox |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 0.17 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere; Reflux 2.1: ammonium chloride; iron / water; isopropyl alcohol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 0.17 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere; Reflux 2.1: ammonium chloride; iron / water; isopropyl alcohol / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine at 50℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62 %Chromat. | With 2-ethynyl-thiophene; tert.-butylnitrite; tris(2,2'-bipyridyl)ruthenium dichloride In N,N-dimethyl-formamide at 20℃; for 10h; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 10h; Sealed tube; Irradiation; regioselective reaction; | |
90 %Chromat. | With tris[2-phenylpyridinato-C2,N]iridium(III); tert.-butylnitrite In acetonitrile at 20℃; Irradiation; regioselective reaction; | 1-20 0.1 mmol of 2- (pyridine-3-yl) aniline (1a) and 0.15 mmol of 2-ethynylthiophene (2a) were prepared as reactants. Prize 0.2 mol of MeCN was added to the reaction mixture, and tert-butyl nitrite (tBuONO) 15 Under 1 mol% of Ru (bpy) 3Cl2, at room temperature, LED was irradiated and reacted. Through this, 51% of 5- (Thiophen-2-yl) benzo [f] quinoline (3aa) (3aa ') and 30% of the demineralized product (4a). Also, 5. And, The yields are shown in Table 1 (Experimental Example 1-1). Here, the yield was measured using gas chromatography |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 81 %Chromat. 2: 7 %Chromat. | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 10h; Sealed tube; Irradiation; regioselective reaction; | |
1: 71 %Chromat. 2: 16 %Chromat. | With tert.-butylnitrite; tris(2,2'-bipyridyl)ruthenium dichloride In tetrahydrofuran at 20℃; for 10h; Sealed tube; Irradiation; regioselective reaction; | |
1: 76 %Chromat. 2: 7 %Chromat. | With tris[2-phenylpyridinato-C2,N]iridium(III); tert.-butylnitrite In acetonitrile at 20℃; Irradiation; | 1-24 0.1 mmol of 2- (pyridine-3-yl) aniline (1a) and 0.15 mmol of 2-ethynylthiophene (2a) were prepared as reactants. Prize 0.2 mol of MeCN was added to the reaction mixture, and tert-butyl nitrite (tBuONO) 15 Under 1 mol% of Ru (bpy) 3Cl2, at room temperature, LED was irradiated and reacted. Through this, 51% of 5- (Thiophen-2-yl) benzo [f] quinoline (3aa) (3aa ') and 30% of the demineralized product (4a). Also, 5. And, The yields are shown in Table 1 (Experimental Example 1-1). Here, the yield was measured using gas chromatography |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 55 %Chromat. 2: 10 %Chromat. 3: 28 %Chromat. | With tert.-butylnitrite; tris(1,10-phenanthroline)ruthenium(II) dichloride In acetonitrile at 20℃; for 10h; Sealed tube; Irradiation; regioselective reaction; | |
1: 55 %Chromat. 2: 10 %Chromat. 3: 28 %Chromat. | With tert.-butylnitrite; tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 10h; Irradiation; | 1-9 0.1 mmol of 2- (pyridine-3-yl) aniline (1a) and 0.15 mmol of 2-ethynylthiophene (2a) were prepared as reactants. Prize 0.2 mol of MeCN was added to the reaction mixture, and tert-butyl nitrite (tBuONO) 15 Under 1 mol% of Ru (bpy) 3Cl2, at room temperature, LED was irradiated and reacted. Through this, 51% of 5- (Thiophen-2-yl) benzo [f] quinoline (3aa) (3aa ') and 30% of the demineralized product (4a). Also, 5. And, The yields are shown in Table 1 (Experimental Example 1-1). Here, the yield was measured using gas chromatography |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; Sealed tube; Irradiation; Overall yield = 80 %; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14 %Chromat. | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris[2-phenylpyridinato-C2,N]iridium(III); tert.-butylnitrite In acetonitrile Irradiation; regioselective reaction; | 2-2 General procedure: As shown in the following Table 2, each of the reactants (aniline compound: 0.5 mmol and heteroalkane compound: 0.75 mmol) , 1.5 eq of tBuONO and 0.3 mol% of fac-Ir (ppy) 3, MeCN (1.0 M) Polyheteroaro Marticidal compounds were synthesized. The respective compound structural formulas and yields are shown together in Table 2 below |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile Irradiation; Overall yield = 77 %; | 3 1a and 2c described in Table 2 were synthesized under various conditions described in Table 4 below to obtain 3ac and 3ac '. 1a and 2c was added 0.3 mol% of photocatalyst fac-Ir (ppy) 3, and the blue LED was irradiated under MeCN to synthesize 3ac and 3ac ' The ratios and the total yields were obtained and are shown together in Table 4 below. 30 and 31 show that Abs and |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
680 mg | With sodium hydrogencarbonate In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium <i>tert</i>-butylate; tris(para-trifluoromethyl)phenyl phosphine In N,N-dimethyl-formamide at 150℃; for 24h; Sealed tube; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With pyridine at 120℃; for 1h; Microwave irradiation; | 123 Example 123 (0570) N1,N1-dimethyl-N4-(2-(pyridin-3-yl)phenyl)benzene-l, 4-disulfonamide A solution of 2-(pyridin-3-yl)aniline (0.170 g, 1.000 mmol) in pyridine (Volume: 2.000 ml) was treated with 4-(N,N-dimethylsulfamoyl)benzene-l-sulfonyl chloride (0.284 g, 1 mmol). The solution was microwaved at 120°C for 1 hr. The product was purified by reversed-phase chromatography (4-100% CH3CN over 15 min) to give desired product (0.013g, 6% yield). (LCMS, ESI pos.) Calculated for C19H19N3O4S2: 418.5 (M + H), Measured: 418.1. NMR (400 MHz, DMSO-i 6) d 10.16 (s, 1H), 8.62 (dd, J= 5.0, 1.6 Hz, 1H), 8.55 (d, J= 2.2 Hz, 1H), 7.93 - 7.85 (m, 3H), 7.81 - 7.73 (m, 2H), 7.55 (dd, J = 7.9, 5.0 Hz, 1H), 7.47 - 7.39 (m, 3H), 7.06 (dt, J= 6.3, 1.7 Hz, 1H), 2.70 (s, 6H). |
Tags: 177202-83-4 synthesis path| 177202-83-4 SDS| 177202-83-4 COA| 177202-83-4 purity| 177202-83-4 application| 177202-83-4 NMR| 177202-83-4 COA| 177202-83-4 structure
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
[ 1258629-77-4 ]
3-(4-Aminophenyl)pyridin-4-amine
Similarity: 0.97
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