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CAS No. : | 3883-39-4 | MDL No. : | MFCD08703184 |
Formula : | C8H9N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LCFYCLRCIJDYQD-UHFFFAOYSA-N |
M.W : | 119.16 | Pubchem ID : | 12503355 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
43% | tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 120℃; for 18.0h; | Step 1: Preparation of 5-methyl-2-vinylpyridine To a solution of 3 g (17.4 mmol) of 2-bromo-5-methylpyridine in 30 ml of dimethylformamide was successively added 2 g (1.7 mmol) of tetrakis (triphenylphosphine)palladium and 5.52 g (17.4 mmol) of tributyl(vinyl)tin. The reaction mixture was stirred at 120C for 18 hours. After cooling, the reaction mixture was poured into 50 ml of water saturated with potassium fluoride and stirred for 1 hour. The mixture was filtered on supersel and the aqueous phase was extracted with ethyl ether. The organic phase was washed twice with water saturated with potassium fluoride, once with water and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give 3.5 g of a crude mixture as a yellow oil. The mixture was purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 4/1) to give 5-methyl-2-vinylpyridine as a yellow oil: 0.9 g (43%); mass spectrum: 120 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With N-benzyl-trimethylammonium hydroxide; at 200℃; for 3.0h; | Step 2: Preparation of 2-[2-(5-methyl-2-pyridinyl)ethyl]-1-H-isoindole-1,3(2H)-dione 0.5 g (4.2 mmol) of <strong>[3883-39-4]5-methyl-2-vinylpyridine</strong> and 0.618 g (4.2 mmol) of phthalimide was added to 0.5 ml of benzyltrimethylammonium hydroxide (Triton B) and the mixture was heated at 200C for 3 hours. The mixture was allowed to cool to room temperature and was directly purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 5/1) to give 2-[2-(5-methyl-2-pyridinyl)ethyl]-1H-isoindole-1,3(2H)-dione as white crystals: 0.680 g (59%); mass spectrum: 267 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 2.0h; | Step 2; To a stirred solution of <strong>[3883-39-4]5-methyl-2-vinylpyridine</strong> (600 mg, 1.87 mmol) in dry CH2CI2 (6 mL) was added N-benzyl-1-methoxy-N- ((trimethylsilyl)methyl)methanamine (1.42 g, 6.0 mmol) and TFA (570 mg, 5.0 mmol) at 00C. The mixture was stirred at rt for 2 TLC showed the disappearance of starting material. The mixture was quenched with satd aq NaHCO3 (15 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column on silica cartridge eluted with PE/EA=5:1 to afford 2-(1-benzyl-pyrrolidin-3-yl)-5-methyl-pyridine (450 mg, 35%) as a yellow oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.6% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃;Inert atmosphere; | Step 1; To a stirred mixture of 2-bromo-5-methyl-pyridine (1.7 g, 10 mmol), 2,4,6- trivinyl-cyclotriboroxanein (1.20 g, 5 mmol) and Na2CO3 (3.73 g, 35.2 mmol) in toluene (15 mL) / EtOH (10 mL) / H2O (5 mL) was added Pd(PPh3)4 (300 mg, 0.25 mmol) under N2. The mixture was stirred at 100 0C overnight. The resulting mixture was quenched with water (20 mL) and extracted with EtOAc (30 mL x 3).The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column (PE:EA=50:1 ) to afford 5-methyl-2-vinyl-pyridine (900 mg, 75.6%) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; at 100℃; for 2.0h;Inert atmosphere; | To a stirred solution of 2-bromo-5-methylpyridine (23.8 g, 138.0 mmol) and potassium vinyl trifluoroborate (20.39 g, 152.0 mmol) in dioxane (235 mL) under nitrogen was added Pd(dppf)2Cl2 (11.30 g, 13.8 mmol), cesium carbonate (135.0 g, 415.0 mmol), and water (41.5 mL). The resulting mixture heated to 100C for 2 hours. The reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 0-30% ethyl acetate/ hexane gradient gave E-1 as a volatile oil, which was carried on directly to next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In toluene; at 100℃; for 3.0h; | To a stirred solution of E-1 (16.44 g, 138.0 mmol) in toluene (300 mL) was added ethyl diazoacetate (42.9 ml, 414.0 mmol) and the resulting mixture was heated to 100C for 3 hours. The mixture was allowed to cool and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 0-20% ethyl acetate/ hexane gradient gave E-2-trans as an oil. (1 1.7 g, 41%). LRMS (ES) (M+H)+ : observed = 206.2, calculated = 206.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | In neat (no solvent); at 170℃; for 0.75h;Microwave irradiation; | General procedure: Both the requisitesulfonamide (1.5 eqv) and 2-vinylpyridine (1.0 eqv) were added to a microwavevial equipped with stir bar. The vial was irradiated in the microwave for 45 minutes(170 C at a maximum of 60 W) after which the crude reaction mixture was dissolvedin acetone, transferred to a round-bottom flask and concentrated via rotary evaporation.The resultant brown residue was dissolved in a minimal amount of hot chloroformand cooled in an ice bath. The excess sulfonamide precipitate was accordingly removedvia filtration, and the filtrate concentrated under vacuum. Subsequently, the residuewas redissolved in a minimal amount of hot chloroform, and then triturated withcold hexanes until a sticky residue formed and the mother liquor remained a cloudywhite color. The mother liquor containing excess 2-vinylpyridine was decanted,while the sticky residue was recrystallized from ethyl acetate/hexanes to affordthe desired product. In some examples, column chromatography (0-75% ethyl acetate/hexanes)was required to thoroughly remove 2-vinylpyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dipotassium hydrogenphosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triphenylphosphine; In dichloromethane; water; at 20℃;Inert atmosphere; Irradiation; | Firstly weighing (27.2 mg, 0.2 mmol),photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6(2.3 mg, 0.002 mmol), K2HPO4(7.0 mg, 0.04 mmol), and Ph3P (62.9 mg, 0.24 mmol) are added to a reaction tube, pumping air through the vacuum line three times, in the argon atmosphere, adding DCM/H2O (2.0 ml, 4:1 v/v), then carefully added (31.5 mg, 0.3 mmol), hen put into 5 W blue LEDs lamp irradiation, react at room temperature for 36 - 60 h. Add 20 ml water, and the DCM extraction (3x 10 ml) the aqueous phase, combined with the organic phase. The organic phase by absolute Na2SO4 after drying and steaming and to remove the solvent, dry sample, column chromatography (300 - 400 item of chromatographic analysis silica gel) (petroleum ether - ethyl acetate) to obtain the product 30.6 mg, Yield 64%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃; for 12.0h;Inert atmosphere; | General procedure: Typically, quinazolinone (0.5 mmol, 73.0 mg), 2-vinylpyridine (1.0 mmol, 105.0 mg), Sc(OTf)3 (0.05 mmol, 24.6 mg) were charged sequentially into the flask with 3 mL toluene. The flask was then evacuated under reduced pressure, followed by the attachment of a nitrogen balloon. The resulting mixture was stirred at 110 for 12 h. The progress of the reaction was monitored by TLC. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel (EA/MeOH = 250:1 150:1) to give the product 3a (103 mg, 82 %) as a white solid. 3-(2-(pyridin-2-yl)ethyl)quinazolin-4(3H)-one (3a). The title compound was prepared according to the general procedure as described above in 82 % yield as white powder, 103 mg. |
A1373868[ 2682115-63-3 ]
5-Methyl-2-vinylpyridine hydrochloride
Reason: Free-salt
[ 17755-52-1 ]
2-(2-(Pyridin-3-yl)vinyl)pyridine
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[ 17755-52-1 ]
2-(2-(Pyridin-3-yl)vinyl)pyridine
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