Home Cart 0 Sign in  
X

[ CAS No. 134296-07-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 134296-07-4
Chemical Structure| 134296-07-4
Chemical Structure| 134296-07-4
Structure of 134296-07-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 134296-07-4 ]

Related Doc. of [ 134296-07-4 ]

Alternatived Products of [ 134296-07-4 ]

Product Details of [ 134296-07-4 ]

CAS No. :134296-07-4 MDL No. :MFCD11042462
Formula : C11H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :QFALAWXXCSQWDH-UHFFFAOYSA-N
M.W :184.19 Pubchem ID :11095276
Synonyms :

Safety of [ 134296-07-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 134296-07-4 ]

* 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.

  • Downstream synthetic route of [ 134296-07-4 ]

[ 134296-07-4 ] Synthesis Path-Downstream   1~79

  • 2
  • [ 134296-07-4 ]
  • [ 149775-41-7 ]
YieldReaction ConditionsOperation in experiment
94% With sodium tetrahydroborate In methanol at 0℃; for 0.25h;
80% With sodium tetrahydroborate In diethyl ether at 0℃; for 0.25h; Inert atmosphere;
49% With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate In 1,2-dichloro-ethane at 20℃; [2,20-Bipyridin]-6-ylmethanol (16) To a solution of 15 (0.10 g,0.54 mmol) in 1,2-dichloroethane was added sodium triacetylborohydride(0.23 g, 1.1 mmol) and the resulting mixturewas stirred atroom temperature overnight. After completion of starting materialchecked with TLC, the mixture was washed with sat. NaHCO3(25 mL), brine (25 mL) and dried with Na2SO4. The crude alcoholwas concentrated and purified by column chromatography toafford pure 16 (eluent system: 50% EA in petroleum, 50 mg, 49%). 1HNMR (300 MHz, CDCl3) d ppm 4.54 (br. s.,1 H, OH), 4.78 (s, 2 H, CH2),7.18e7.29 (m, 2 H, Py), 7.66e7.78 (m, 2 H, Py), 8.21 (d, J 7.9 Hz, 1 H,Py), 8.27e8.34 (m, 1 H, Py), 8.57e8.65 (m, 1 H, Py). 13C NMR(75 MHz, CDCl3) d ppm 64.12 (1 C, CH2), 119.48 (1 C, Py), 120.32 (1 C,Py), 120.96 (1 C, Py), 123.65 (1 C, Py), 136.79 (1 C, Py), 137.45 (1 C,Py), 148.99 (1 C, Py), 154.62 (1 C, Py), 155.51 (1 C, Py), 158.65 (1 C,Py). HRMS (ESI): m/z [M H] Calcd. for [C11H10N2O H]187.0866, found 187.0855
With sodium tetrahydroborate In methanol at 0℃; for 0.25h; Yield given;

  • 3
  • [ 56100-22-2 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
34.1% With selenium(IV) oxide; water; In 1,4-dioxane; for 3h;Resolution of racemate; A mixture of compound 1 (3.31 g, 19.45 mmol) and selenium dioxide (1.27 g, 11.5 mmol) in dioxane (50 mL) containing H2O (0.21 mL) was refluxed for 3 h. After the foregoing mixture was cooled to room temperature, additional selenium dioxide (1.27 g, 11.5 mmol) and H2O (0.2 mL) were added and then the mixture was refluxed for 27 h. The hot reaction mixture was filtered and the insoluble material was washed with warm dioxane and ethyl acetate (20 mL * 3). The crude product was purified by column chromatography to give the title compound (1.28 g, 34.1%) as colourless oil. 1H NMR (400 MHz, CDCl3) delta ppm: 10.18 (s, 1H), 8.74 (ddd, J = 4.8, 1.7, 0.9 Hz, 1H), 8.65 (dd, J = 7.1, 1.95 Hz, 1H), 8.56 (d, J = 7.9 Hz, 1H), 7.97-8.02 (m, 2H), 7.90 (td, J = 7.9, 1.8 Hz, 1H), 7.40 (ddd, J = 7.1, 4.8, 1.1 Hz, 1H). 13C NMR (100 MHz, CDCl3) delta ppm: 193.7, 156.6, 155.0, 152.3, 149.3, 138.0, 137.1, 125.3, 124.4, 121.5, 121.4. ESI-MS (m/z): calcd for C11H8N2O [M + H]+ 185.20, found 185.15.
31% With selenium(IV) oxide; water; In 1,4-dioxane; at 101℃; for 30h;Inert atmosphere; Methyl-2,2 & ' -bipyridine, 3.31 g,Selenium dioxide, 3.24 grams,Water 0.21 ml,Were dissolved in 50 ml of dioxane,Heated to reflux for 3 hours,Again, 3.24 g of selenium dioxide and 0.21 ml of water were added,Heated to reflux for 27 hours,After cooling to room temperature,The solvent was distilled off,Using methylene chloride: methanol = 15: 1 as developing solvent,Column separation,Pure product III 1.28 g was obtained,Yield 31%.
  • 4
  • [ 134296-07-4 ]
  • (E)-1,2-Bis-[2,2']bipyridinyl-6-yl-ethene-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With sodium cyanide In ethanol for 2h; Heating;
  • 5
  • 6-(1,3-dioxolan-2-yl)-2,2'-bipyridine [ No CAS ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 60℃; for 3h; Yield given;
  • 6
  • [ 1121-60-4 ]
  • [ 134296-07-4 ]
  • [ 134842-12-9 ]
  • (E)-1-[2,2']Bipyridinyl-6-yl-2-pyridin-2-yl-ethene-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium cyanide In ethanol for 2h; Heating; Title compound not separated from byproducts;
  • 7
  • [ 134296-07-4 ]
  • [ 212914-81-3 ]
  • 6-(1,3,7,11-Tetrathia-cyclotetradec-2-ylidenemethyl)-[2,2']bipyridinyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With n-butyllithium In tetrahydrofuran at -60℃;
  • 8
  • [ 149775-41-7 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Swern oxidation; Yield given;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 25℃; for 1h; Inert atmosphere; 15 Example 15: Synthesis of [2,2'-bipyridine]-6-carbaldehyde (2,2'-bipyridine-6-carbaldehyde) (Formula 19) Anhydrous CH2C12 (5 mL) followed by oxalyl chloride (3.07g, 24.19 mmol) was introduced through a syringe in a flame dried two-necked round bottom flask equipped with rubber septum and nitrogen balloon and magnetic spin bar and contents cooled to -78 °C. DMSO (3.77g, 48.38 mmol) was added and contents stirred for 15 min. A solution of 6-hydroxymethyl-2,2'-bipyridine (2g, 10.75 mmol) in 5 mL CH2C12 and after 5 min, Et3N (4.88g, 48.38 mmol) were added. The cooling bath was removed and the reaction mixture allowed to warm to 25 °C and stirring continued at this temperature for another 1 Hr. The solvent was removed on a rotary evaporator under reduced pressure at 45°C and the contents extracted with ethyl acetate. The organic layer was washed with saturated aqueous Na2C03 followed by saturated brine solution and dried over anhydrous Na2S04. After removal of the solvent under reduced pressure on rotary evaporator, the crude product was purified by column chromatography. (0286) 1H NMR (300 MHz, CDC13): δ = 10.16 (s, 1H), 8.68 (ddd, 1H, = 4.82, 1.72, 1.03 Hz), 8.62 (dd, 1H, = 5.85, 2.75 Hz), 8.51 (ddd, 1H, = 7.91, 1.03, 0.69 Hz), 7.98-7.92 (m, 2H), 7.83 (dt, 1H, = 7.57, 1.72 Hz), 7.33 (ddd, 1H, = 7.57, 4.82, 1.03 Hz). 13C NMR (75 MHz, CDC13): δ = 193.75, 156.74, 155, 152.38, 149.39, 138, 137.15, 125.22, 124.39, 121.47, 121.38.
  • 9
  • [ 134296-07-4 ]
  • [ 94-41-7 ]
  • 6-(1,4-dioxo-2,4-diphenylbutyl)-2,2'-bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; sodium t-butanolate In ethanol at 90℃; for 20h;
  • 10
  • [ 127-09-3 ]
  • [ 56100-22-2 ]
  • [ 134296-07-4 ]
  • [ 82740-75-8 ]
  • 11
  • [ 134296-07-4 ]
  • [ 187262-57-3 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 6-formyl-2,2'-bipyridine With sodium cyanide Stage #2: With iodine
Multi-step reaction with 2 steps 1: 91 percent / aq. NaCN / ethanol / 2 h / Heating 2: 53 percent / I2 / CH2Cl2 / 3 h / 25 °C
  • 12
  • [ 366-18-7 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: MeI / acetonitrile / 45 °C 1.2: K3Fe(CN)6 / aq. NaOH / 5 °C 1.3: Br2; PPh3 / acetonitrile / 0 °C 2.1: 75 percent / n-BuLi
Multi-step reaction with 2 steps 1.1: diethyl ether / 16 h / -78 - 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: selenium(IV) oxide / 1,4-dioxane / 30 h / Reflux
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 5 h / 0 °C / Inert atmosphere; Reflux 2: selenium(IV) oxide; water / 1,4-dioxane / 3 h / Resolution of racemate
Multi-step reaction with 2 steps 1: diethyl ether / 5 h / 0 °C / Inert atmosphere; Reflux 2: selenium(IV) oxide; water / 1,4-dioxane / 30 h / 101 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 36 h / 25 °C 2: N,N-Dimethylcarbamoyl chloride / dichloromethane / 48 h / 25 °C 3: hydrogenchloride; water / 48 h / 80 °C 4: sodium tetrahydroborate / tetrahydrofuran / 2 h / 80 °C 5: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 - 25 °C / Inert atmosphere

  • 13
  • [ 134296-07-4 ]
  • C23H16N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaCN 1.2: 48 percent / I2 2.1: 41 percent / NH4OAc / acetic acid / microwave irradiation
  • 14
  • [ 134296-07-4 ]
  • C29H20N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaCN 1.2: 48 percent / I2 2.1: 48 percent / NH4OAc / acetic acid / microwave irradiation
  • 15
  • [ 134296-07-4 ]
  • [ 499969-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride; t-BuONa / ethanol / 20 h / 90 °C 2: 504 mg / NH4OAc / ethanol / 42 h / 90 °C
  • 16
  • [ 134296-07-4 ]
  • C17H19N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: NaIO4 / CH2Cl2; H2O / Ambient temperature
  • 17
  • [ 134296-07-4 ]
  • [ 210771-39-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) KCN, 2.) I2 / 1.) EtOH, H2O, reflux, 2 h, 2.) CH2Cl2, 25 deg C, 15 h 2: ethanol / 2 h / Heating 3: chloranil / xylene / 16 h / Heating
  • 18
  • [ 134296-07-4 ]
  • 6-(3-Pyridin-2-yl-5,6-dihydro-pyrazin-2-yl)-[2,2']bipyridinyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) KCN, 2.) I2 / 1.) EtOH, H2O, reflux, 2 h, 2.) CH2Cl2, 25 deg C, 15 h 2: ethanol / 2 h / Heating
  • 19
  • [ 34160-40-2 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / p-TsOH / benzene / 48 h / Heating 2: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -20 deg C, 10 min; -40 deg C, 15 min, 2.) -40 deg C to r.t., overnight 3: 2 M aq. HCl / 3 h / 60 °C
Multi-step reaction with 2 steps 1: Acidic conditions 2: n-butyllithium
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / methanol / 4 h / Reflux; Inert atmosphere; Schlenk technique 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 0.17 h / -78 °C / Schlenk technique; Inert atmosphere 2.3: 36 h / 50 °C / Schlenk technique; Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 60 °C / Inert atmosphere; Schlenk technique
  • 20
  • [ 134296-07-4 ]
  • [ 187262-58-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 91 percent / aq. NaCN / ethanol / 2 h / Heating 2: 53 percent / I2 / CH2Cl2 / 3 h / 25 °C 3: ethanol / 1.5 h / Heating 4: chloranil / xylene / 16 h / Heating
  • 21
  • [ 134296-07-4 ]
  • C24H18N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 91 percent / aq. NaCN / ethanol / 2 h / Heating 2: 53 percent / I2 / CH2Cl2 / 3 h / 25 °C 3: ethanol / 1.5 h / Heating
  • 22
  • [ 134296-07-4 ]
  • [ 187262-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 91 percent / aq. NaCN / ethanol / 2 h / Heating 2: 53 percent / I2 / CH2Cl2 / 3 h / 25 °C 3: 67 percent / ethanol / 1 h / Heating
  • 23
  • [ 134296-07-4 ]
  • [ 187262-60-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / aq. NaCN / ethanol / 2 h / Heating 2: 30 percent / NH4OAc / 2 h / 180 °C
  • 24
  • [ 34199-87-6 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -20 deg C, 10 min; -40 deg C, 15 min, 2.) -40 deg C to r.t., overnight 2: 2 M aq. HCl / 3 h / 60 °C
  • 25
  • [ 134296-07-4 ]
  • [ 162238-21-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: molecular sieves 4 Angstroem / Candida antarctica lipase / diisopropyl ether / 5 h / Ambient temperature
  • 26
  • [ 626-05-1 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) n-BuLi / 1) Et2O, hexane, THF, -78 deg C, 2) THF, -78 deg C, 5 min 2: 1) n-BuLi / 1) Et2O-hexane-THF, -78 deg C, 5-10 min, 2) -78 deg C
Multi-step reaction with 3 steps 1: n-butyllithium 2: Acidic conditions 3: n-butyllithium
  • 27
  • [ 134296-07-4 ]
  • [ 83478-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 0.25 h / 0 °C 2: 90 percent / CBr4, Ph3P / CH2Cl2 / 0 °C
  • 28
  • [ 10495-73-5 ]
  • butyllithium-in-hexane [ No CAS ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydrogencarbonate; In N-methyl-acetamide; diethyl ether; EXAMPLE 5 6-Formyl-2,2'-bipyridine (compound known from Aust. J. Chem. 44 (1991), 331) A solution of 7.05 g (30 mmol) of <strong>[10495-73-5]6-bromo-2,2'-bipyridine</strong> in 50 ml of diethyl ether is added to a solution of 19.4 ml (31 mmol) of 1.6M butyllithium-in-hexane solution in 100 ml of diethyl ether at -80 C. under a nitrogen atmosphere. After the addition is complete, stirring is carried out for a further 30 minutes at this temperature, after which a solution of 4.39 g (60 mmol) of dimethylformamide in 30 ml of diethyl ether is added at from -80 to -90 C. After further stirring at this temperature for 1.5 hours, hydrolysis is carried out with 150 ml of quarter-concentrated hydrochloric acid at from -60 to -50 C. The reaction mixture is then neutralized at room temperature by adding solid sodium bicarbonate, the phases are separated and the aqueous phase is extracted once again with 50 ml of diethyl ether. The organic phases are combined and are dried over sodium sulfate and finally the solvent is distilled off under reduced pressure. The title compound is obtained as a reddish brown oil which crystallizes on standing. Yield: 96% of theory, mp.=41-43 C.
  • 29
  • [ 4073-98-7 ]
  • [ 134296-07-4 ]
  • bis{((6-pyridin-2-yl)pyridin-2-ylmethyleneamino)-3,5-dimethylphenyl}methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% formic acid; In ethanol; for 24h;Heating / reflux; To a suspension of 2,2'-bipyridinyl-6-carbaldehyde (0.38 g, 2.07 mmol) in absolute ethanol (5 ml) was added 2a (0.13 g, 0.52 mmol, 0.25 eq. ) and one drop of formic acid. The orange solution was heated to reflux for 24 hours. On cooling to 0 °C the suspension was filtered, washed with cold diethyl ether (100 ml) and dried under reduced pressure to give 25 as yellow solid (0.22 g, 71percent). Compound 25: ES mass spectrum, m/z 587 [M+H]+. 1H NMR (CDCl3), 2.14 (s, 12H, Ar-CH3), 3.53 (s, 2H, CH2), 6.89 (s, 4H, Ar-H), 7.21 (dd, 2H, 3J(HH) 6.1, 4J(HH) 1.2, Py-H), 7.72 (td, 2H, 3J(HH) 7.8, 4J(HH) 1.6, Py-H), 7.86 (t, 2H, 3J(HH) 7.8, Py-H), 8.21 (dd, 2H, 3J(HH) 7.8 Hz, 4J(HH) 0.9, Py-H), 8.34 (s, 2H, HC=N), 8.41 (d, 2H, 3J(HH) 7.8, Py-H), 8.44 (dd, 2H, 3J(HH) 7.4, 4J(HH) 0.9, Py-H), 8.60 (dd, 2H, 3J(HH) 4.5,4J(HH) 0.7, Py-H).
  • 30
  • [ 54827-17-7 ]
  • [ 134296-07-4 ]
  • 3,5,3',5'-tetramethyl-N,N-bis{(6-pyridin-2-yl)pyridin-2-ylmethylene}biphenyl-4,4'-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% formic acid; In diethyl ether; for 48h;Heating / reflux; To a suspension of 2,2'-bipyridinyl-6-carbaldehyde (0.39 g, 2.10 mmol) in diethyl ether (5 ml) was added la (0.13 g, 0.53 mmol, 0.25 eq. ) and one drop of formic acid. The yellow reaction mixture was heated to reflux for 48 hours. On cooling to room temperature the suspension was filtered, washed with cold diethyl ether and dried under reduced pressure to give 15 as a yellow solid (0.10 g, 34%). Compound 15: ES mass spectrum, m/z 573 [M+H]+. ¹H NMR (CDCl3), delta 2.18 (s, 12H, (Ar-CH3)), 7.29 (s, 4H, Ar-H), 7.41 (dd, 2H, 3J(HH) 6.7, 4J(HH) , Py-H), 7.75 (td, 2H, 3J(HH) 7.8, 4J(HH) 1.8, Py-H), 7.90 (t, 2H, 3J(HH) 7.8, Py-H), 8.27 (dd, 2H, 3J(HH) 7.8, 4J (HH) 1.6, Py-H), 8.40 (s, 2H, HC=N), 8.44 (dd, 2H, 3J(HH) 7.5, 4J(HH) 1.2, Py- H), 8.46 (dd, 2H, 3J(HH) 7.4, 4J(HH) 0.9, Py-H), 8.62 (dd, 2H, 3J(HH) 4.3, 4J(HH) 0.7, Py-H).
  • 31
  • [ 186703-54-8 ]
  • [ 134296-07-4 ]
  • 3,5,3',5'-tetraisopropyl-N,N-bis{(6-pyridin-2-yl)pyridin-2-ylmethylene}biphenyl-4,4'-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% In diethyl ether for 24h; Heating / reflux; 25 To a mixture of 2,2'-bipyridinyl-6-carbaldehyde (0.39 g, 2.10 mmol) in diethyl ether (5 ml) was added 1b (0.18 g, 0.53 mmol, 0.25 eq. ) and one drop of formic acid. The orange solution was heated to reflux for 24 hours. On cooling to 0 °C the suspension was filtered, washed with cold diethyl ether and dried under reduced pressure to give 16 as yellow solid (0.20 g, 51 %). Compound 16: ES mass spectrum, m/z 685 [M+H] (at); ¹H NMR (CDCl3), δ 1.20 (d, 24H, 3J(HH) 6.9, CH(CH3)), 2.81 (sept, 4H, CH(CH3)2), 7.17 (s, 4H, Ar-H), 7.41 (dd, 2H, 3J(HH) 6.7, 4J(HH) 1.6, Py-H), 7.75 (td, 2H, 3J(HH) 7.8, 4J(HH) 1.8, Py-H), 7.90 (t, 2H, 3J (HH) Py-H), 8.27 (dd, 2H, 3 J(HH) 7.8, 4J (HH) 1.6, CH), 8.40 (s, 2H, HC=N), 8.44 (dd, 2H, 3J(HH) 7.5, 4J(HH) 1.2, Py-H), 8.46 (dd, 2H, 3J(HH) 7.4, 4J(HH) 0.9, Py-H), 8.62 (dd, 2H, 3J(HH) 4.3, 4J(HH) 0.7, Py-H); ¹3C NMR (CDCl3, ¹H gated decoupled), δ 22.5 (s, CH3), 27.2 (s, CH), 120.1 (s, Ar), 120.3 (s, Ar), 121.0 (s, Ar), 121.6 (s, Ar), 122.9 (s, Ar), 129.2 (s, Ar), 136.0 (s, Ar), 136.6 (s, Ar), 137.1 (s, Ar), 146.6 (s, Ar), 148.0 (s, Ar), 153.0 (s, Ar), 154.7 (s, Ar), 155.1 (s, Ar), 162.5 (s, C=N).
  • 32
  • [ 3102-87-2 ]
  • [ 134296-07-4 ]
  • 2,3,5,6-tetramethyl-N,N-bis{(6-pyridin-2-yl)pyridin-2-ylmethylene}benzene-1,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% formic acid; In ethanol; for 48h;Heating / reflux; To a suspension of 2,2'-bipyridinyl-6-carbaldehyde (0.39 g, 2.10 mmol) in diethyl ether (5 ml) was added 2,3,5,6-tetramethyl-benzene-1,4-diamine (0.086 g, 0.52 mmol, 0.25 eq. ) and one drop of formic acid. The orange solution was heated to reflux for 48 hours. On cooling to 0 C, the suspension was filtered, washed with cold ethanol and dried under reduced pressure to give 12a as a yellow solid (0.08 g, 31%). Compound 12a: ES mass spectrum, m/z 497 [M+H]+; ¹H NMR (CDCl3), delta 2.08 (s, 12H, Ar-CH3), 7.26 (qd, 2H, 3J(HH) 6.1, 4J(HH) 1.1, Py-H), 7.76 (td, 2H, 3J(H-H) 7.8, 4J(HH) 1.6, Py-H), 7.90 (t, 2H, 3J(HH) 7.9, Py-H), 8.29 (dd, 2H, 3J(HH) 7.8, 4J(HH) 0.9, Py-H), 8.34 (s, 2H, HC=N), 8.43 (d, 2H, 3J(HH) 7.8, Py-H), 8.45 (dd, 2H, 3J(HH) 7.8, 4J(HH) 0.9, Py-H), 8.64 (d, 2H, 3J(HH) 3.9, Py-H); ¹3C NMR (CDCl3, ¹H gated decoupled), delta 14.1 (s, Ar-CH3), 119.9 (s, Ar), 120.2 (s, Ar), 121.5 (s, Ar), 122.4 (s, Ar), 122.9 (s, Ar), 136.0 (s, Ar), 136.6 (s, Ar), 146.4 (s, Ar), 148.3 (s, Ar), 153.2 (s, Ar), 154.7 (s, Ar), 155.0 (s, Ar), 163.3 (s, C=N).
  • 33
  • [ 19900-69-7 ]
  • [ 134296-07-4 ]
  • bis{((pyridin-2-yl)pyridin-2-ylmethyleneamino)-3,5-diisopropylphenyl}methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In ethanol for 24h; Heating / reflux; 36 To a suspension of 2,2'-bipyridinyl-6-carbaldehyde (0.39 g, 2.09 mmol) in absolute ethanol (5 ml) was added 2b (0.19 g, 0.53 mmol, 0.25 eq. ) and one drop of formic acid. The brown solution was heated to reflux for 24 hours. On cooling to 0 °C, the suspension was filtered, washed with cold ethanol and dried under reduced pressure to give 26a as a brown solid (0.19 g, 52%). Compound 26a: ES mass spectrum, m/z 699 [M+H]+; IR (cm-1), 1640 1580, 1547 (C=N) ; ¹H NMR (CDCl3), δ 1.07 (d, 12H, 3J (HH) 6.7, CH (CH3)2), 1.10 (d, 12H, 3J(HH) 6.8, CH (CH3)2), (sept, 4H, CH(CH3)2), 3.28 (s, 2H, CH2), 6.95 (s, 4H, Ar- H), 7.21 (qd, 2H, 3J(HH) 6.1, 4J(HH) 1.2 Hz, Py-H), 7.72 (td, 2H, 3J(HH) 7.8, 4J(HH) 1.8, Py-H), 7.86 (t, 2H, 3J(HH) 7.8, Py-H), 8.21 (dd, 2H, 3J(HH) 7.8, 4J(HH) 0.9, Py- H), 8.34 (s, 2H, HC=N), 8.41 (d, 2H, 3J(HH) 7.8, Py-H), 8.44 (dd, 2H, 3J(HH) 7.4, 4J(HH) 0.9, Py-H), 8.60 (dd, 2H, 3J(HH) 4.5, 4J(HH) 0.7, Py-H) ; ¹3C NMR (CDCl3, ¹H gated decoupled), δ 22.5 (s, CH3), 27.0 (s, CH3), 29.3 (s, CH), 40.6 (s, CH2), 120.0 (s, Ar), 120.2 (s, Ar), 121.6 (s, Ar), 122.7 (s, Ar), 122.9 (s, Ar), 135.9 (s, Ar), 136.3 (s, Ar), 136.5 (s, Ar), 145.5 (s, Ar), 148.2 (s, Ar), 153.0 (s, Ar), 154.6 (s, Ar), 155.0 (s, Ar), 162.1 (s, Ar), 162.5 (s, C=N).
  • 34
  • [ 34160-40-2 ]
  • [ 882521-96-2 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
  • 37
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 29841-69-8 ]
  • [ 5970-45-6 ]
  • [ 134296-07-4 ]
  • (Zn(N2C10H7CHN2H2C2H2(C6H5)2)2)(2+)*2PF6(1-)*2H2O=(Zn(N2C10H7CHN2H2C2H2(C6H5)2)2)(PF6)2*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.4% In methanol to soln. 1,2-diphenyl-1,2-diaminoethane and 2,2'-bipyridine-6-carbaldehyde in MeOH FeCl2*4H2O was added at room temp., stirred for 1 h, NH4PF6 was added dropwise; ppt. was filtered, washed with water, dissolved in MeCN, filtered and evapd., residue was dried in vacuo over P2O5; wlem. anal.;
  • 38
  • [ 67-56-1 ]
  • [ 134296-07-4 ]
  • [ 18531-95-8 ]
  • C44H36N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With acetic acid In dichloromethane at 20℃; diastereoselective reaction;
  • 39
  • ammonium hexafluorophosphate [ No CAS ]
  • iron(II) chloride tetrahydrate [ No CAS ]
  • [ 20439-47-8 ]
  • [ 134296-07-4 ]
  • Fe2((C5H4NC5H3NCHN)2C6H10)2(4+)*4PF6(1-)*2.5H2O=(Fe2((C5H4NC5H3NCHN)2C6H10)2)(PF6)4*2.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.4% In methanol; water cyclohexane-compd. and bipyridine-compd. dissolved in MeOH, solid Fe-compd. added to the stirred solution at room temp., stirred for 1 h, aq. NH4PF6 added dropwise, allowed to stand for 1 h; filtered by suction, washed with MeOH/H2O (v/v, 1:5), redissolved in CH3CN, filtered, solv. removed in vac., dried in vac. over P2O5, elem. anal.;
  • 40
  • ammonium hexafluorophosphate [ No CAS ]
  • iron(II) chloride tetrahydrate [ No CAS ]
  • [ 21436-03-3 ]
  • [ 134296-07-4 ]
  • Fe2((C5H4NC5H3NCHN)2C6H10)2(4+)*4PF6(1-)*2.5H2O=(Fe2((C5H4NC5H3NCHN)2C6H10)2)(PF6)4*2.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In methanol; water cyclohexane-compd. and bipyridine-compd. dissolved in MeOH, solid Fe-compd. added to the stirred solution at room temp., stirred for 1 h, aq. NH4PF6 added dropwise, allowed to stand for 1 h; filtered by suction, washed with MeOH/H2O (v/v, 1:5), redissolved in CH3CN, filtered, solv. removed in vac., dried in vac. over P2O5, elem. anal.;
  • 41
  • [ 67-56-1 ]
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 20439-47-8 ]
  • [ 5970-45-6 ]
  • [ 134296-07-4 ]
  • Zn2((C5H4NC5H3NCHN)2C6H10)2(4+)*4PF6(1-)*2CH3OH*2H2O=(Zn2((C5H4NC5H3NCHN)2C6H10)2)(PF6)4*2CH3OH*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In methanol; water cyclohexane-compd. and bipyridine-compd. dissolved in MeOH, solid Zn-compd. added to the stirred solution at room temp., stirred for 1 h, aq. NH4PF6 added dropwise, allowed to stand for 1 h; filtered by suction, washed with MeOH/H2O (v/v, 1:5), redissolved in CH3CN, filtered, solv. removed in vac., dried in vac. over P2O5, elem. anal.;
  • 42
  • [ 848135-09-1 ]
  • [ 134296-07-4 ]
  • [ 1286707-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol 2: sodium tetrahydroborate / 1-methyl-pyrrolidin-2-one; ethanol
  • 43
  • [ 1454-80-4 ]
  • [ 134296-07-4 ]
  • [ 1286707-44-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol 2: sodium tetrahydroborate / 1-methyl-pyrrolidin-2-one; ethanol
  • 44
  • [ 4488-22-6 ]
  • [ 134296-07-4 ]
  • [ 1197213-12-9 ]
  • 45
  • [ 4488-22-6 ]
  • [ 134296-07-4 ]
  • [ 1286707-50-3 ]
  • 46
  • 2,2'-diamino-6,6'-dimethylbiphenyl [ No CAS ]
  • [ 134296-07-4 ]
  • [ 1286707-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol 2: sodium tetrahydroborate / 1-methyl-pyrrolidin-2-one; ethanol
  • 47
  • carbonic acid bis(1-isopropylhydrazide) dihydrochloride [ No CAS ]
  • [ 134296-07-4 ]
  • [ 1319745-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium acetate / methanol / Reflux 2: p-benzoquinone / toluene / 1 h / Reflux; under air
  • 48
  • carbonic acid bis(1-isopropylhydrazide) dihydrochloride [ No CAS ]
  • [ 134296-07-4 ]
  • [ 1319745-02-2 ]
YieldReaction ConditionsOperation in experiment
1.628 g With sodium acetate In methanol Reflux;
  • 49
  • [ 134296-07-4 ]
  • N,N'-bis(2,2'-bipyridin-6-ylmethyl)pentane-1,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 0.17 h / Reflux 2: sodium tetrahydroborate / methanol / 2 h
  • 50
  • [ 134296-07-4 ]
  • [ 928292-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 0.17 h / Reflux 2: sodium tetrahydroborate / methanol / 2 h
Multi-step reaction with 2 steps 1: methanol / 3 h 2: sodium tetrahydroborate / methanol / 1 h
  • 51
  • [ 134296-07-4 ]
  • [ 107-15-3 ]
  • C24H20N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol for 0.5h; Reflux;
In methanol for 2h; 1 Synthesis of compound (2) (en-bpy2) 2,2'-bipyridine-6-carboxaldehyde 0.20g (1.1 × 10-3mol) and ethylene diamine 0.04g (6.5 × 10-4mol) were mixed in methanol, stirring was carried out for 2 hours . Then, to give a yellow powder under reduced pressure to dryness.
  • 53
  • [ 3731-51-9 ]
  • [ 134296-07-4 ]
  • [ 1402046-07-4 ]
YieldReaction ConditionsOperation in experiment
68% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 5h; Inert atmosphere;
  • 54
  • [ 3731-51-9 ]
  • [ 134296-07-4 ]
  • [ 1402045-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
  • 55
  • [ 134296-07-4 ]
  • [ 1539-42-0 ]
  • [ 1339945-49-1 ]
YieldReaction ConditionsOperation in experiment
41% Stage #1: 6-formyl-2,2'-bipyridine; bis[(2-pyridyl)methyl]amine With thionyl chloride In methanol for 2h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol for 3h; Inert atmosphere;
  • 56
  • 4,4'-dimethyl-1,1'-biphenyl-2,2'6,6'-tetraamine [ No CAS ]
  • [ 134296-07-4 ]
  • N,N',N'',N'''-tetrakis(2,2'-bipyridin-6-ylmethyl)-4,4'-dimethyl-1,1'-biphenyl-2,2',6,6'-tetraamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.6% With sodium tetrahydroborate In ethanol for 6h; Inert atmosphere; Schlenk technique; Reflux;
  • 57
  • [ 109-04-6 ]
  • [ 34199-87-6 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
80% With nickel(II) chloride hexahydrate; iodine; acetic acid; lithium chloride; zinc In N,N-dimethyl-formamide at 50 - 70℃; for 6h;
  • 58
  • [ 134296-07-4 ]
  • [ 107-15-3 ]
  • C24H20N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.9% In methanol
  • 59
  • [ 35160-98-6 ]
  • [ 134296-07-4 ]
  • 6-[2-(benzo[c]phenanthren-2-yl)vinyl]-2,2'-bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: (benzo[g]phenanthren-3-ylmethyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.75h; Schlenk technique; Inert atmosphere; Stage #2: 6-formyl-2,2'-bipyridine In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Schlenk technique; Inert atmosphere;
  • 60
  • [ 35160-95-3 ]
  • [ 134296-07-4 ]
  • C22H16N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: (2-naphthalenylmethyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.75h; Schlenk technique; Inert atmosphere; Stage #2: 6-formyl-2,2'-bipyridine In tetrahydrofuran; hexane at -78 - 20℃; Schlenk technique; Inert atmosphere;
  • 61
  • [ 34160-40-2 ]
  • [ 17997-47-6 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In 1,4-dioxane at 180℃; for 0.25h; Microwave irradiation; Generalprocedure for Stille coupling. General procedure: A G10vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or 6-bromopyridinecarbonitrile (89 mg, 0.479 mmol, 1 eq), CuI (15 mg, 0.048mmol, 0.1 eq), Pd(PPh3)2Cl2 (28mg, 0.048mmol,0.1 eq), 2-(tributylstannyl) pyridine (278 uL, 0.527 mmol, 1.1 eq)and 6 ml of dioxane. The resulting mixture was irradiated using the closedvessel mode at 180°C for 15 min. The reaction mixture was filtered through apad of alumina with diethyl ether. The crude product was purified by flashchromatography on silica gel, with a pentane/AcOEt (95/5) as the eluent.
40% With tetrakis(triphenylphosphine) palladium(0) In toluene Reflux; [2,20-Bipyridine]-6-carbaldehyde (15) According to a literatureprocedure [53], a solution of 6-bromo-2-pyridinecarboxaldehyde (0.20 g, 1.1 mmol), 2-(tributylstannyl)pyridine (0.37 g, 1.0 mmol)and tetrakis(triphenylphosphine)palladium (41 mg, 0.035 mmol) indegased tolune (20 mL) was refluxed overnight under nitrogen. Thevolatile in the resulting brown mixture was removed in vacuo. Thecrude aldehyde was purified by column chromatography to afford15 (eluent system: 25% EA in petroleum, 74 mg, 40%). 1H NMR(300 MHz, CDCl3) d ppm 7.30e7.39 (m, 1 H, Py), 7.80e7.88 (m, 1 H,Py), 7.91e7.98 (m, 2 H, Py), 8.49e8.55 (m, 1 H, Py), 8.59e8.65 (m,1 H, Py), 8.66e8.71 (m, 1 H, Py), 10.15 (s, 1 H, CHO). 13C NMR(75 MHz, CDCl3) d ppm 121.18 (1 C, Py), 121.30 (1 C, Py), 124.23 (1 C,Py), 125.05 (1 C, Py), 136.99 (1 C, Py), 137.83 (1 C, Py), 149.22 (1 C,Py), 152.20 (1 C, Py), 154.85 (1 C, Py), 156.55 (1 C, Py), 193.56 (1 C,CHO). HRMS (ESI): m/z [M H] Calcd. for [C11H8N2O H]185.0710, found 185.0696.
  • 62
  • [ 2627-86-3 ]
  • [ 134296-07-4 ]
  • (S)-N-([2,2'-bipyridin]-6-ylmethyl)-1-phenylethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: (<i>S</i>)-1-phenyl-ethylamine; 6-formyl-2,2'-bipyridine With magnesium sulfate In dichloromethane at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 20℃; General procedure for reductive amination. General procedure: To astirred solution of amine (1 eq) and MgSO4 (2 eq), dichloromethane orTHF (1 mL per 0.1 mmol) was added the carboxaldehyde derivative (1 eq). Themixture is stirred at room temperature for 2 h. After filtration and concentratedunder vacuum, MeOH (1 mL per 0.1 mmol) and NaBH4 (3eq) were added. Thereaction mixture was stirred at room temperature for 2h. The solution was thenconcentrated under vacuum and 10 mL of saturated aqueous solution of NH4Clwas added, the aqueous phase was extracted with EtOAc (3 x 10 mL). The combinedlayers were dried (MgSO4), filtered and concentrated under vacuum.The crude product was purified by flash chromatography on silica gel withpentane/AcOEt (7/3 to 1/1) as the eluent.
  • 63
  • [ 10420-89-0 ]
  • [ 134296-07-4 ]
  • (S)-N-([2,2'-bipyridin]-6-ylmethyl)-1-(naphthalen-1-yl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: (S)-1-(1-Naphthyl)ethylamine; 6-formyl-2,2'-bipyridine With magnesium sulfate In dichloromethane at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 20℃; General procedure for reductive amination. General procedure: To astirred solution of amine (1 eq) and MgSO4 (2 eq), dichloromethane orTHF (1 mL per 0.1 mmol) was added the carboxaldehyde derivative (1 eq). Themixture is stirred at room temperature for 2 h. After filtration and concentratedunder vacuum, MeOH (1 mL per 0.1 mmol) and NaBH4 (3eq) were added. Thereaction mixture was stirred at room temperature for 2h. The solution was thenconcentrated under vacuum and 10 mL of saturated aqueous solution of NH4Clwas added, the aqueous phase was extracted with EtOAc (3 x 10 mL). The combinedlayers were dried (MgSO4), filtered and concentrated under vacuum.The crude product was purified by flash chromatography on silica gel withpentane/AcOEt (7/3 to 1/1) as the eluent.
  • 64
  • [ 134296-07-4 ]
  • [ 74317-53-6 ]
  • 2-(2,2'-bipyridin-6-ylmethyleneamino)-3',6'-bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.1% for 6h; Reflux; 2.3 2.2.3 Synthesis of 2-(2,2'-bipyridin-6-ylmethyleneamino)-3',6'-bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one (RBP) A mixture of Rhodamine B hydrazide (0.547 g, 1.14 mmol) and 2,2'-bipyridine-6-carbaldehyde (0.184 g, 1.00 mmol) in ethanol (20 mL) was refluxed for 6 h. The pure RBP as a yellow solid (0.36 g, 50.1%) was obtained by column chromatography. 1H NMR (400 MHz, CDCl3) δ ppm: 8.84 (s, 1H), 8.31-8.60 (m, 2H), 7.70-8.03 (m, 3H), 7.31-7.62 (m, 4H), 7.15 (d, J = 8.3 Hz, 1H), 6.55 (t, J = 8.4 Hz, 1H), 6.46 (d, J = 7.7 Hz, 2H), 6.42 (d, J = 7.8 Hz, 2H), 6.23-6.32 (m, 2H), 3.33 (q, J = 7.0 Hz, 8H), 1.15 (t, J = 6.9 Hz, 12H). 13C NMR (100 MHz, CDCl3) δ ppm: 166.2, 153.8, 149.0, 148.9, 148.8, 136.9, 136.8, 132.5, 128.1, 127.9, 120.8, 120.5, 108.0, 105.9, 104.5, 97.9, 97.9, 66.2, 65.9, 44.3, 12.6. ESI-MS (m/z): calcd for C39H38N6O2 [M + H]+ 623.3134, found 623.3174.
50% In ethanol at 78℃; for 6h; Inert atmosphere; 3 Example 3
Synthesis of the fluorescent probe of the present invention (Figure 4) A mixture of 0.18 g of 6-aldehyde-2,2'-bipyridine,Rhodamine B hydrazide 0.55 g,Was dissolved in 20 ml of ethanol,The mixture was heated under reflux for 6 hours.The product was isolated on an alkaline silica gel column,Dichloromethane as developing solvent,0.362 g of pure product probe was obtained,Yield 50%. Nuclear magnetic resonance
  • 65
  • [ 134296-07-4 ]
  • [ 82740-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C 2: thionyl chloride / 2 h / Inert atmosphere; Reflux
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / diethyl ether / 0.25 h / 0 °C / Inert atmosphere 2: thionyl chloride / 2 h / 0 °C / Reflux; Inert atmosphere
  • 66
  • [ 109-04-6 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - -70 °C / Inert atmosphere; Schlenk technique 1.2: -78 - 40 °C / Inert atmosphere; Schlenk technique 2.1: toluene-4-sulfonic acid / methanol / 4 h / Reflux; Inert atmosphere; Schlenk technique 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 3.2: 0.17 h / -78 °C / Schlenk technique; Inert atmosphere 3.3: 36 h / 50 °C / Schlenk technique; Inert atmosphere 4.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 60 °C / Inert atmosphere; Schlenk technique
  • 67
  • [ 128507-76-6 ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 0.17 h / -78 °C / Schlenk technique; Inert atmosphere 1.3: 36 h / 50 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 60 °C / Inert atmosphere; Schlenk technique
  • 68
  • 6-(dimethoxy)methyl-2,2'-bipyridine [ No CAS ]
  • [ 134296-07-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In tetrahydrofuran; water at 60℃; for 4h; Inert atmosphere; Schlenk technique;
  • 69
  • [ 134296-07-4 ]
  • [ 4848-43-5 ]
  • C25H24N3P [ No CAS ]
  • 70
  • [ 134296-07-4 ]
  • [ 177263-77-3 ]
  • C30H26N3P [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 6-formyl-2,2'-bipyridine; (2-(diphenylphosphanyl)phenyl)methanamine In methanol at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With sodium tetrahydroborate In methanol at 20℃; Inert atmosphere; Schlenk technique;
  • 71
  • [ 134296-07-4 ]
  • [ 105-56-6 ]
  • C16H13N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In ethanol
  • 72
  • [ 1290085-12-9 ]
  • [ 134296-07-4 ]
  • C26H28N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium sulfate In dichloromethane at 20℃;
  • 73
  • N,N′-bis(2′,6′-diisopropylphenyl)-1-amino-perylene-3,4:9,10-tetracarboxylic acid bisimide [ No CAS ]
  • [ 134296-07-4 ]
  • N,N′-bis(2′,6′-diisopropylphenyl)-13-(2″,2‴-bipyridin-6″-yl)-azabenzo[pqr]-perylene-3,4:9,10-tetracarboxylic acid bisimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: N,N′-bis(2′,6′-diisopropylphenyl)-1-amino-perylene-3,4:9,10-tetracarboxylic acid bisimide; 6-formyl-2,2'-bipyridine With trifluoroacetic acid In N,N-dimethyl-formamide at 110℃; for 0.5h; Molecular sieve; Schlenk technique; Inert atmosphere; Stage #2: With oxygen In N,N-dimethyl-formamide at 110℃; Molecular sieve; Schlenk technique;
  • 74
  • [ 35132-20-8 ]
  • [ 134296-07-4 ]
  • [ 103-71-9 ]
  • (2S,4R,5R)-2-([2,2′-bipyridin]-6-yl)-N′,4,5-triphenylimidazolidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: (R,R)-1,2-diphenylethylenediamine; 6-formyl-2,2'-bipyridine In ethyl acetate at 20℃; for 0.0833333h; Molecular sieve; Stage #2: phenyl isocyanate In ethyl acetate at 20℃; for 0.0833333h; Molecular sieve; Stage #3: With sodium tetrahydroborate In methanol; ethyl acetate at 20℃; for 0.333333h; Molecular sieve;
  • 75
  • [ 134296-07-4 ]
  • [ 50476-18-1 ]
  • bis-(pyrazolyl)bipyridinylmethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
2 g With cobalt(II) chloride at 75℃; for 48h; Inert atmosphere;
  • 76
  • [ 134296-07-4 ]
  • [ 87023-84-5 ]
  • bis(3,5-methylpyrazolyl)bipyridinylmethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
13.8 g With cobalt(II) chloride at 75℃; for 48h; Inert atmosphere;
  • 77
  • [ 134296-07-4 ]
  • N-[([2,2'-bipyridin]-6-yl)methylidene]hydroxylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydroxylamine hydrochloride In ethanol for 0.5h; Reflux; 45 Example 45: Synthesis of N-[([2,2'-bipyridin]-6-yl)methylidene]hydroxylamine (Formula 49) A solution of 2,2'-bipyridine-6-carbaldehyde (0.5 g, 2.71mmol), hydroxylamine hydrochloride (1.87g, 27.17 mmol) and pyridine (2.1g, 27.17 mmol) in 10 mL ethanol was refluxed for 30 min. The solvents were removed under reduced pressure, water (10 mL) added and contents extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine, dried over Na2S04 and evaporated under reduced pressure on a rotary evaporator at 45 °C to leave a residue, which was re-crystallised from methanol. (0366) 1H NMR (300 MHz, CDCI3): δ = 8.69 (ddd, 1H, = 4.82, 1.72, 1.03 Hz), 8.45 (ddd, 1H, = 7.91, 1.03, 0.69 Hz), 8.38 (dd, 1H, = 6.88, 1.72 Hz), 8.34 (s, 1H), 7.87 -7.79 (m, 3H), 7.33 (ddd, 1H, J = 7.57, 4.82, 1.03 Hz). 13C NMR (300 MHz, CDC13): δ = 156.05, 155.72, 151.35, 149.25, 137.51, 137.16, 124.04, 121.54, 121.44, 120.79. Calculated Mass: 199.0746, Observed Mass: 199.0938.
  • 78
  • [ 134296-07-4 ]
  • 6,6'-[hydrazinediylidenedimethanylylidene]di(2,2'-bipyridine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In methanol for 0.5h; 73 Example 73: Synthesis of 6,6'-[hydrazinediylidenedimethanylylidene]di(2,2'-bipyridine) (Formula 77) Hydrazine hydrate (6.75 mg, 0.135 mmol) was added to solution of 2,2'-bipyridine-6- carboxaldehyde (50 mg, 0.27 mmol) in methanol (1 mL) and contents stirred for 30 min, when the desired compound precipitated out as colorless solid. (0447) 1H NMR (300 MHz, CDC13): δ = 8.77 (s, 2H), 8.70 (ddd, 2H, 7 = 4.82, 1.72, 1.03 Hz), 8.53-8.48 (m, 4H), 8.21 (dd, 2H, 7 = 7.91, 1.03 Hz), 7.93 (t, 2H, 7 = 7.91 Hz), 7.85 (td, 2H, 7 = 7.57, 1.75 Hz), 7.34 (ddd, 2H, 7 = 7.57, 4.82, 1.38 Hz). 13C NMR (75 MHz, CDCI3): δ = 162.28, 156.36, 155.71, 152.63, 149.3, 137.53, 137.07, 124.06, 122.5, 121.97, 121.35 ppm. Calculated Mass: 364.1436, Observed Mass: 364.1622.
  • 79
  • [ 920-39-8 ]
  • [ 134296-07-4 ]
  • [ 864544-21-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran for 0.25h; Inert atmosphere; 17 Example 17: Synthesis of 1-([2,2'-bipyridin]-6-yl)-2-methylpropan-1-one (Formula 21) A solution of 2,2'-Bipyridine-6-carbaldehyde (0.4 g, 2.17 mmol) in anhydrous THF (10 niL) was introduced through a syringe in a flame dried two-necked round bottom flask equipped with rubber septum and nitrogen balloon and magnetic spin bar. Isopropylmagnesium bromide (0.958g, 6.52 mmol) was added to the solution and contents stirred for 15 min. Saturated aqueous Na2C03 solution was added to the reaction mixture and contents extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine solution and dried over sodium sulphate. The solvents were removed on a rotary evaporator under reduced pressure at 45 °C to yield product as oil. The alcohol product, without purification was subjected to swern oxidation following a procedure similar to that described in Example 15. (0290) 1H NMR (300 MHz, CDC13): δ = 8.69 (ddd, 1H, 7 = 4.82 , 1.72, 1.03 Hz), 8.60 (dd, 1H, 7 = 7.91, 1.03 Hz), 8.51 (ddd, 1H, 7 = 7.91, 1.03, 0.69 Hz), 8.05 (dd, 1H, 7 = 7.57, 1.38 Hz), 7.95 (dd, 1H, 7 = 7.91, 7.57 Hz), 7.86 (dt, 1H, 7 = 7.91, 1.72 Hz) 7.35 (ddd, 1H, 7 = 7.57, 4.82, 1.03 Hz), 4.28 (sep, 1H, 7 = 6.88 Hz), 1.27 (d, 6H, 7 = 6.88 Hz). 13C NMR (75 MHz, CDC13): δ = 205.82, 155.59, 155.28, 152.23, 149.3, 138, 137.11, 124.18, 124.15, 122.39, 121.19, 34.51, 18.86.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 134296-07-4 ]

Aldehydes

Chemical Structure| 211382-46-6

[ 211382-46-6 ]

6'-Methyl-[2,2'-bipyridine]-6-carbaldehyde

Similarity: 1.00

Chemical Structure| 108295-42-7

[ 108295-42-7 ]

[2,2':6',2''-Terpyridine]-6-carbaldehyde

Similarity: 1.00

Chemical Structure| 327994-98-9

[ 327994-98-9 ]

6'-Ethynyl-[2,2'-bipyridine]-6-carbaldehyde

Similarity: 0.89

Chemical Structure| 108295-45-0

[ 108295-45-0 ]

[2,2':6',2''-Terpyridine]-4'-carbaldehyde

Similarity: 0.84

Chemical Structure| 138253-30-2

[ 138253-30-2 ]

4-([2,2':6',2''-Terpyridin]-4'-yl)benzaldehyde

Similarity: 0.83

Related Parent Nucleus of
[ 134296-07-4 ]

Pyridines

Chemical Structure| 211382-46-6

[ 211382-46-6 ]

6'-Methyl-[2,2'-bipyridine]-6-carbaldehyde

Similarity: 1.00

Chemical Structure| 108295-42-7

[ 108295-42-7 ]

[2,2':6',2''-Terpyridine]-6-carbaldehyde

Similarity: 1.00

Chemical Structure| 327994-98-9

[ 327994-98-9 ]

6'-Ethynyl-[2,2'-bipyridine]-6-carbaldehyde

Similarity: 0.89

Chemical Structure| 108295-45-0

[ 108295-45-0 ]

[2,2':6',2''-Terpyridine]-4'-carbaldehyde

Similarity: 0.84

Chemical Structure| 138253-30-2

[ 138253-30-2 ]

4-([2,2':6',2''-Terpyridin]-4'-yl)benzaldehyde

Similarity: 0.83