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[ CAS No. 764-48-7 ] {[proInfo.proName]}

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Chemical Structure| 764-48-7
Chemical Structure| 764-48-7
Structure of 764-48-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 764-48-7 ]

CAS No. :764-48-7 MDL No. :MFCD00192151
Formula : C4H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VUIWJRYTWUGOOF-UHFFFAOYSA-N
M.W : 88.11 Pubchem ID :12995
Synonyms :

Calculated chemistry of [ 764-48-7 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.11
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : 0.14
Log Po/w (MLOGP) : -0.33
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : 0.32

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.28
Solubility : 46.6 mg/ml ; 0.529 mol/l
Class : Very soluble
Log S (Ali) : -0.32
Solubility : 42.6 mg/ml ; 0.484 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.2
Solubility : 55.7 mg/ml ; 0.632 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 764-48-7 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:3271
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 764-48-7 ]

* 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 [ 764-48-7 ]

[ 764-48-7 ] Synthesis Path-Downstream   1~78

  • 1
  • [ 764-48-7 ]
  • [ 292638-85-8 ]
  • [ 41440-38-4 ]
YieldReaction ConditionsOperation in experiment
25% With 1,4-diaza-bicyclo[2.2.2]octane; 10H-phenothiazine; zinc diacetate; oxygen; 4-methoxy-phenol; at 75 - 83℃; for 2h; Rotor,thermometer,Gas introduction pipe,In a 100 milliliter flask equipped with a condenser tube,21.60 parts (0.2451 mol) of ethylene glycol monovinyl ether,37.97 parts (0.4413 mol) of methyl acrylate,0.2750 parts (0.0025 mol) of DABCO as the catalyst A,0.8997 parts (0.0049 mol) of zinc acetate as the catalyst B,0.0304 parts of hydroquinone monomethyl ether (500 wt ppm with respect to the total weight of the charged raw materials)0.0015 part (25 wt ppm based on the total weight of the charged raw materials) of phenothiazine was charged,While bubbling an oxygen-containing gas (5% by volume of oxygen and 95% by volume of nitrogen) into the solution, heating and stirring was carried out for 2 hours at a reaction solution temperature in the range of 75 to 83 C.after that,When methanol contained in the reaction solution was quantified,The reaction yield was 25%
  • 2
  • [ 764-48-7 ]
  • [ 920-46-7 ]
  • [ 1464-69-3 ]
YieldReaction ConditionsOperation in experiment
In to a reactor, 3.79 parts of the compound represented by formula (I-2-a), 10 parts of tetrahydrofuran and 4.79 parts of triethylamine were charged and stirred at 23 C. for 30 minutes. The obtained mixture was cooled into 0 C. Then, 4.50 parts of the compound represented by formula (I-1-b) was dropped thereto over 30 minutes at 0 C., and the obtained mixture was stirred for 1 hour at 0 C. 100 parts of ethyl acetate, 50 parts of ion exchanged water and 50 parts of a saturated aqueous ammonium chloride solution were added to the resulting reactant, the obtained mixture was stirred at 23 C. for 30 minutes, and left still to separate an organic layer. To the obtained organic layer, 100 parts of ion exchanged water was added, stirred at 23 C. for 30 minutes, and left still, followed by separating an organic layer to wash with water. The washing step was conducted five times. The obtained organic layer was concentrated and purified with column chromatography [silica gel 60N spherical shape, neutral, 100-210 mum, solvent: mixture of n-heptane/ethyl acetate=5/I, manufactured by Kanto Chem. Ltd.], to provide 3.12 parts of the compound represented by formula (I-2-c).
3.79 parts of the compound represented by the formula (I-2-a), 10 parts of tetrahydrofuran and 4.79 parts of triethylamine were added, followed by stirring at 23 C. for 30 minutes and cooling to 0 C.To the resulting mixture, 4.50 parts of the compound represented by the formula (I-2-b) was added dropwise over 30 minutes at 0 C. and further stirred at 0 C. for 1 hour.To the obtained reaction product, 100 parts of ethyl acetate, 50 parts of ion-exchanged water and 50 parts of a saturated aqueous solution of ammonium chloride were added, and the mixture was stirred at 23 C. for 30 minutes, and the mixture was allowed to stand and liquids were separated.100 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 C. for 30 minutes, and the organic layer was washed with water by allowing to stand and separating.This washing operation was repeated 5 times.The recovered organic layer was concentrated, and the concentrated mass was separated by column (Kanto Chemical silica gel 60 N (spherical, neutral) 100-210 mum developing solvent: n-heptane / ethyl acetate = 5/1) -2-c) was obtained.
  • 3
  • [ 764-48-7 ]
  • [ 98-59-9 ]
  • [ 99051-18-0 ]
YieldReaction ConditionsOperation in experiment
95.46% With triethylamine; In dichloromethane; at 0 - 20℃; for 4h; To a solution of 2-vinyloxyethanol (4.0 g, 45.4 mmol) and TEA (12.66 mL, 90.8 mmol) in dichloromethane (50 mL) was added 4-methylbenzene-l-sulfonyl chloride (12.98 g, 68.1 mmol) at 0 C and the mixture was then stirred at room temperature for 4 hour. After the reaction was completed, the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with petroleum ether: EtOAc = 50:1-5:1) to give 2- vinyloxyethyl 4-methylbenzenesulfonate (10.5 g, 95.46%). MS obsd. (ESI+) [(M+H)+]:243.l.
  • 4
  • [ 764-48-7 ]
  • [ 542-58-5 ]
YieldReaction ConditionsOperation in experiment
51% With sulfuryl dichloride for 2h; Ambient temperature;
  • 5
  • [ 764-48-7 ]
  • [ 110-75-8 ]
  • [ 764-99-8 ]
YieldReaction ConditionsOperation in experiment
66.3% With sodium hydroxide; tributyl-amine at 90℃; for 8h;
  • 7
  • [ 764-48-7 ]
  • [ 28075-50-5 ]
  • 2-(1-cyclohexen-1-yl)-2-methyl-1,3-dioxolane [ No CAS ]
  • 8
  • [ 764-48-7 ]
  • [ 115375-59-2 ]
  • 2-(3,4-dihydro-6-methoxy-1-naphthyl)-2-methyl-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 1,3-bis-(diphenylphosphino)propane; triethylamine In dimethyl sulfoxide for 0.0833333h; Irradiation;
  • 9
  • [ 764-48-7 ]
  • [ 424788-79-4 ]
  • 1,1-(ethylenedioxy)-3-hydroxy-5-methoxyindan [ No CAS ]
  • 10
  • [ 4595-59-9 ]
  • [ 764-48-7 ]
  • 2-(pyrimid-5-ylmethyl)-1,3-dioxolane [ No CAS ]
  • 11
  • [ 5332-24-1 ]
  • [ 764-48-7 ]
  • 2-(quinol-3-ylmethyl)-1,3-dioxolane [ No CAS ]
  • 2-(1-quinol-3-ylvinyloxy)ethanol [ No CAS ]
  • 12
  • [ 1120-87-2 ]
  • [ 764-48-7 ]
  • 4-((1,3-dioxolan-2-yl)methyl)pyridine [ No CAS ]
  • 2-[1-(pyrid-4-yl)vinyloxy]ethanol [ No CAS ]
  • 13
  • [ 764-48-7 ]
  • [ 348-61-8 ]
  • 2-(3,4-difluorophenyl)-2-methyl-1,3-dioxolane [ No CAS ]
  • 2-(3,4-difluorobenzyl)-1,3-dioxolane [ No CAS ]
  • 14
  • [ 764-48-7 ]
  • [ 392-83-6 ]
  • 2-methyl-2-[2-(trifluoromethyl)phenyl]-1,3-dioxolane [ No CAS ]
  • 2-[2-(trifluoromethyl)benzyl]-1,3-dioxolane [ No CAS ]
  • 15
  • [ 764-48-7 ]
  • [ 623-00-7 ]
  • [ 14517-91-0 ]
  • 4-(1,3-dioxolan-2-ylmethyl)benzonitrile [ No CAS ]
  • 16
  • [ 764-48-7 ]
  • [ 2042-37-7 ]
  • 2-(2-cyanobenzyl)-1,3-dioxolane [ No CAS ]
  • 2-[1-(2-cyanophenyl)-vinyloxy]ethanol [ No CAS ]
  • 17
  • [ 764-48-7 ]
  • [ 402-43-7 ]
  • [ 30993-34-1 ]
  • 2-methyl-2-[(4-trifluoromethyl)phenyl]-1,3-dioxolane [ No CAS ]
  • 18
  • [ 764-48-7 ]
  • [ 99-90-1 ]
  • [ 105752-35-0 ]
  • 2-(4-acetylbenzyl)-1,3-dioxolane [ No CAS ]
  • 19
  • [ 764-48-7 ]
  • [ 1122-91-4 ]
  • [ 14490-45-0 ]
  • 2-(4-formylbenzyl)-1,3-dioxolane [ No CAS ]
  • 20
  • [ 764-48-7 ]
  • [ 586-78-7 ]
  • [ 19073-15-5 ]
  • [ 134485-50-0 ]
  • 21
  • [ 764-48-7 ]
  • [ 5459-93-8 ]
  • [ 84761-77-3 ]
  • 3-(N-cyclohexyl-N-ethylamino)-1,1-(ethylenedioxy)indan [ No CAS ]
  • 22
  • [ 764-48-7 ]
  • [ 344-38-7 ]
  • 2-methyl-2-[4-nitro-3-(trifluoromethyl)phenyl]-1,3-dioxolane [ No CAS ]
  • 2-[4-nitro-3-(trifluoromethyl)benzyl]-1,3-dioxolane [ No CAS ]
  • 26
  • [ 764-48-7 ]
  • [ 99-90-1 ]
  • [ 105752-35-0 ]
YieldReaction ConditionsOperation in experiment
88% With 1,3-bis-(diphenylphosphino)propane; triethylammonium tetrafluoroborate; diisopropylamine;palladium diacetate; In 1-butyl-3-methylimidizolium tetrafluoroborate; at 20 - 115℃; for 2h; C. General procedure for the Heck arylation ofhydroxyalkyl vinyl ethers (le-f)An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 2 (1.0 mmol), Pd(OAc)2 (0.025 mmol), DPPP (0.05 mmol), [HNEt3][BF4] (1.5 mmol), and [bmim] [BF4] (2 mL) under nitrogen at room temperature. Following degassing three times, a hydroxyalkyl vinyl ether 1 (2.0 mmol) and HN1Pr2 (1.5 mmol) were injected sequentially. The flask was placed in an oil bath, and the mixture was stirred and heated at 115 0C. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. A small sample was then taken for NMR analysis. The rest of the mixture was extracted with CH2Cl2 (3 x 20 mL), and the combined organic layer was <n="15"/>washed with water until neutral, dried (Na2SO^, filtered, and concentrated in vacuo. The cyclic ketal derived from the arylated olefin was isolated out of the crude product by flash chromatography on silica gel using a mixture of ethyl acetate and hexane (10/90 to 20/80) containing 2% (in volume) triethylamine as eluant. The isolated yields of the products are given in Table 1.
  • 28
  • [ 626-05-1 ]
  • [ 764-48-7 ]
  • [ 61463-67-0 ]
YieldReaction ConditionsOperation in experiment
1) Production of 2-[(6-bromopyridin-2-yl)oxy]ethanol 8.81 g of ethylene glycol monovinyl ether was added to toluene (100 mL) suspension of 2.4 g of sodium hydride (55% to 72%), and 9.48 g of 2,6-dibromopyridine was added thereto and stirred overnight at 110 C. The reaction liquid was left cooled to room temperature, and water was added thereto to separate the organic layer. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. 100 mL of methanol and 576 mg of p-toluenesulfonic acid hydrate were added to the resulting residue, and stirred for 5 hours. After this was concentrated under reduced pressure, aqueous saturated sodium hydrogencarbonate solution was added to it, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1) to obtain 7.74 g of the entitled compound as a colorless oily substance. 1H-NMR (400 MHz, CDCl3) delta: 7.45 (1H, t, J=7.5 Hz), 7.09 (1H, d, J=7.4 Hz), 6.74 (1H, d, J=8.2 Hz), 4.46 (2H, t, J=4.4 Hz), 3.96 (2H, t, J=4.4 Hz). ESI-MS Found: m/z[M+H]+ 218, 220.
  • 29
  • [ 764-48-7 ]
  • [ 6136-66-9 ]
  • C17H16O3 [ No CAS ]
  • 30
  • [ 764-48-7 ]
  • [ 99-91-2 ]
  • [ 1009-61-6 ]
  • 31
  • [ 3430-31-7 ]
  • [ 764-48-7 ]
  • [ 1072933-63-1 ]
  • 32
  • [ 764-48-7 ]
  • [ 149068-56-4 ]
  • [ 1053172-84-1 ]
YieldReaction ConditionsOperation in experiment
83% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In ethylene glycol at 145℃; Inert atmosphere; regioselective reaction;
  • 33
  • [ 764-48-7 ]
  • [ 1191389-68-0 ]
  • [ 1217841-82-1 ]
YieldReaction ConditionsOperation in experiment
55% 3-bromo-l-(4-methoxyphenyl)-2-phenyl-lH-indole (100 mg, 0.26 mmol), 2- (vinyloxy)ethanol (116 mg, 1.32 mmol), palladium acetate (3 mg, 0.01 mmol), K2CO3 (48 mg, 0.34 mmol) and tetrabutyl ammonium bromide (4 mg, 0.01 mmol) were mixed with toluene (0.5 ml) and water (0.5 ml) in a microwave vial under nitrogen. The reaction was run at 150 0C for 20 min. 2 ml 3M HCl was added and the mixture was stirred at RT for 30 min. Water and DCM were added and the phases were separated. After evaporation of the solvents, the residue was purified by flash chromatography with Heptane/EtOAc 9:1 as eluent, to provide 50 mg (55%) of l-(l-(4-methoxyphenyl)-2-phenyl-lH-indol-3- yl)ethanone.
Steps (a) and (b): 1 eq. 3-Bromo-l -(4-methoxy-phenyl)-2-phenyl-lH-indole (synthesised from l-(4- methoxyphenyl)-lH-indole by a method analogous to that used in steps (a), (b) and (c) of Example 21 followed by steps (a) and (b) of Example 22), 5 eq. ethylene glycol monovinyl ether, 5 mol% Pd(OAc)2, 10 mol% dppp, 1.3 eq. potassium acetate, 5 mol% tetrabutylammonium bromide were mixed with toluene/water in a microwave vial under nitrogen. The reaction was run in a microwave reactor at 150 0C for 20 min. 2 ml 3M HCl was added and the mixture was stirred at RT for 30 min. Water and DCM were added and the phases were separated. After evaporation of the solvents, the residue was purified by flash chromatography with heptane/EtOAc 9: 1.
  • 34
  • [ 764-48-7 ]
  • [ 6386-38-5 ]
  • [ 1234581-60-2 ]
  • 35
  • [ 764-48-7 ]
  • [ 30159-70-7 ]
  • [ 1280733-05-2 ]
  • 36
  • [ 524-38-9 ]
  • [ 764-48-7 ]
  • [ 391212-30-9 ]
YieldReaction ConditionsOperation in experiment
61.4% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; Intermediate 2; O-(2-(vinyloxy)ethyl)hydroxylamine; Step A: 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione To a solution of 2-(vinyloxy)ethanol (20.4 mL, 227 mmol), triphenylphosphine (59.5 g, 227 mmol), and N-hydroxyphthalimide (37.0 g, 227 mmol) in THF (450 mL) was added DEAD (35.9 mL, 227 mmol) at 0 C. under a N2 atmosphere. After stirring for 16 h at room temperature, the reaction mixture was concentrated in vacuo. The residue was filtered, washed with chloroform and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex: EtOAc=2:1) to give 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.5 g, 61.4%) as a yellow solid. 1H NMR (CDCl3, Varian 400 MHz) delta 4.04-4.08 (3H, m), 4.19 (1H, dd, J=14.4, 2.2 Hz), 4.45-4.48 (2H, m), 6.47 (1H, dd, J=14.0, 6.8 Hz), 7.53-7.78 (2H, m), 7.80-7.87 (2 m, m).
  • 37
  • [ 15231-91-1 ]
  • [ 764-48-7 ]
  • [ 10441-41-5 ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; triethylamine; diphenylphosphinopropane; In ethylene glycol; at 145℃; for 4h;Inert atmosphere; 10109] Compound 4a, 1 -(6-hydroxynaphthalen-2-yl)etha-none, was synthesized by the inventors.10110] Specifically, starting materials for synthesis such as6-bromo-2-naphthol (2.0 g, 8.97 mmol), Pd(OAc)2 (100mg,0.45 mmol), DPPP (370 mg, 0.9 mmol), and ethylene glycol (3 mE) were added to an oven-dried flask with two necks and charged with argon gas. Oxygen present in the mixture was removed by adding the argon gas to the resulting mixture, and ethyleneglycolvinylether (2.41 mE, 27 mmol) and Et3N obtained distillation (3.12 mE, 22.4 mmol) were sequentially added. The mixture was stirred at 145 C. for 4 hours using a silicone oil containet The mixture was cooled to room temperature and stirred with dichloromethane (15 mE) and a 5% HC1 aqueous solution (30 mE) at room temperature for 1 hout The resulting mixture was extracted with dichioromethane (2x30 mE), and an organic layer was washed with water (30 mE) and dehydrated with anhydrous sodium sulfate (6 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by column chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using CH2C12 as a developer), thereby obtaining a solid, Compound 4a(1.33 g, 80%).10111] ?H NMR (CDC13, 300 MHz, 298 K, oe): 8.41 (1H, s), 7.98 (1H, dd, J=8.7, 1.6 Hz), 7.87 (1H, d, J=8.7 Hz), 7.70 (1H, d, J=8.7 Hz), 7.16 (1H, dd, J=8.7, 1.6 Hz), 5.4 (1H, s), 2.71 (3H, s); mp 172 C.
  • 38
  • [ 764-48-7 ]
  • [ 1914-59-6 ]
  • 2-oxo-4-phenyl-but-3-enoic acid 2-vinyloxy-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 25℃; General procedure: To a stirred mixture of alcohol, 2-oxo-4-aryl-but-3-enoic acid and DMAP in dichloromethane at 0 C was added dropwise DCC in dichloromethane. After 10 min, the reaction mixture was allowed to warm to room temperature and stirred for 10 h. After filtration of the resulting mixture, solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using CH2Cl2 as eluant.
  • 39
  • [ 764-48-7 ]
  • [ 135248-89-4 ]
  • [ 1497404-36-0 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(N,N'-dimethylenisobutyramidine) dihydrochloride; In acetonitrile; at 20℃; for 0.333333h;pH 4.0;UV-irradiation; Darkness; General procedure: Effect of the concentration of ene compound was investigated following the procedures described in Example 14. Thus, 50 muL of Fmoc-Cys (50 mM in acetonitrile), various amount of Ene Compound 3 (500 mM in pH 4.0 acetate buffer) and 50 muL of VA-044 (50 mM in pH 4.0 acetate buffer) were added in 350 muL of acetate buffer (0.2 M, pH 4.0) in a clear plastic tube at room temperature. The homogenous solution was irritated under 365 nm. The reaction mixtures were monitored and analyzed by HPLC and MS to determine the completeness and product formation, with the results shown in the table below.
  • 40
  • [ 764-48-7 ]
  • [ 6160-65-2 ]
  • O-(2-(vinyloxy)ethyl) 1H-imidazole-1-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In toluene; at 20 - 60℃; For Xanthate 1, in a three-neck round bottom flask equipped with a reflux, 3.6 g of 1,1'- thiocarbonyl diimidazole and 0.05 g (20 mmol) of KOH were dissolved in 60 mL toluene. 1.9 mL (20 mmol) of <strong>[764-48-7]2-hydroxyethyl vinyl ether</strong> (HOVE, donated by Maruzen Petrochemical) was then added and stirred. The mixture was heated at 60 C for about 6 h and left overnight at room temperature with stirring. O-2-(vinyloxy)ethyl 1H-imidazole-1-carbothioate was synthesized during this process. 2.4 mL (20 mmol) of benzyl mercaptan was then added and stirred. The mixture was then continue to heat at 60 C for about 6 h and left overnight at room temperature with stirring. The suspension was filtrated, and the excess toluene was removed by an evaporator. The product was then isolated from residue by column chromatography, using silica gel as stationary phase, with mixture of ethyl acetate and hexane as an eluent (1:10 v/v). The solvent was evaporated to dryness and the yellow product was verified using 1HNMR, 13C NMR, and IR spectroscopy (yield: 60%). 1H NMR (CDCl3,25 C): delta 4.08 and 4.21 (dd, 2H, CH2CHO, J = 2.38 and 2.37 Hz), 6.50 (q, 1H, CH2CHO, J = 6.87 Hz), 4.83 (t, 2H, CH2CH2O, J = 4.65 Hz), 4.03 (t, 2H, CH2CH2O, J = 4.65 Hz), 4.38 (s, 2H, CS2CH2C6H5), 7.23e7.38 (m, 5H, CS2CH2C6H5). 13C NMR (CDCl3, 25 C): delta 40.26, 64.8, 71.12 (all CH2), 87.10 (OCHCH2), 127.30 (phenyl-C4), 128.34 (phenyl-C2), 128.79 (phenyl-C3), 135.27 (phenyl-C1), 150.98 (OCHCH2), 213.41 (CO(S)S). IR (neat, r.t.): 1065, 1191, 1495, 1616 cm-1.
In toluene; at 60℃; for 6h;Reflux; To a round bottom flask 1 L, 1,1'-thiocarbonyldiimidazole 3.6 g (20.2 mmol), <strong>[764-48-7]2-hydroxyethyl vinyl ether</strong> (95% purity) 1.9 mL (20.2 mmol) and toluene 60mL was added, 60 at was refluxed for 6 hours. Then allowed to cool to room temperature, potassium hydroxide 0.05g (0.89mmol) and benzyl mercaptan 2.4mL of (20.5 mmol) was added, and the mixture was refluxed for 6 hours again 60 C.
  • 41
  • [ 764-48-7 ]
  • [ 5324-30-1 ]
  • C10H21O5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; SYNTHESIZE HYDROLYTICALLY STABLE COUPLING AGENT The new coupling agent vinyl glycidyl ethylphosphonic acid (FIG. 9) was synthesized according to the phosphorylation method for compound 10. This agent has a phosphonic group, which can strongly bind with FA and teeth. Only ether moieties instead of esters existing in the entire molecule make it hydrolytically stable.
  • 42
  • [ 455-19-6 ]
  • [ 764-48-7 ]
  • 2-(1,3-dioxolan-2-yl)-1-(4-(trifluoromethyl)phenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 43
  • [ 764-48-7 ]
  • [ 6630-33-7 ]
  • 1-(2-bromophenyl)-2-(1,3-dioxolan-2-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 44
  • [ 764-48-7 ]
  • [ 456-48-4 ]
  • C11H13FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 45
  • [ 764-48-7 ]
  • [ 387-45-1 ]
  • 1-(2-chloro-6-fluorophenyl)-2-(1,3-dioxolan-2-yl)ethanolk [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 46
  • [ 764-48-7 ]
  • [ 6287-38-3 ]
  • 1-(3,4-dichlorophenyl)-2-(1,3-dioxolan-2-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 47
  • [ 764-48-7 ]
  • [ 552-89-6 ]
  • 2-(1,3-dioxolan-2-yl)-1-(2-nitrophenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 48
  • [ 764-48-7 ]
  • [ 555-16-8 ]
  • 2-(1,3-dioxolan-2-yl)-1-(4-nitrophenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 49
  • [ 764-48-7 ]
  • [ 105-07-7 ]
  • 4-(2-(1,3-dioxolan-2-yl)-1-hydroxyethyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 50
  • [ 764-48-7 ]
  • [ 138490-95-6 ]
  • 2-(1,3-dioxolan-2-yl)-1-(2-iodo-3,4-dimethoxyphenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 51
  • [ 764-48-7 ]
  • [ 712-97-0 ]
  • 2-(1,3-dioxolan-2-yl)-1-(6-nitrobenzo[d][1,3]dioxol-5-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 52
  • [ 764-48-7 ]
  • [ 4265-16-1 ]
  • 1-(benzofuran-2-yl)-2-(1,3-dioxolan-2-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 53
  • [ 13669-42-6 ]
  • [ 764-48-7 ]
  • 2-(1,3-dioxolan-2-yl)-1-(quinolin-3-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 54
  • [ 764-48-7 ]
  • [ 27996-86-7 ]
  • 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-2-(1,3-dioxolan-2-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 55
  • [ 104-53-0 ]
  • [ 764-48-7 ]
  • 1-(1,3-dioxolan-2-yl)-4-phenylbutan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 56
  • [ 764-48-7 ]
  • [ 66-25-1 ]
  • 1-(1,3-dioxolan-2-yl)heptan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 57
  • [ 764-48-7 ]
  • [ 100-52-7 ]
  • [ 100058-84-2 ]
YieldReaction ConditionsOperation in experiment
91% General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.
  • 58
  • [ 764-48-7 ]
  • [ 610-71-9 ]
  • 2-(vinyloxy)ethyl 2,5-dibromobenzoate [ No CAS ]
  • 59
  • [ 764-48-7 ]
  • [ 79996-90-0 ]
  • endo-8b-cyano-1-(2-hydroxyethoxy)-4-hydroxymethyl-1,2,2a,8b-tetrahydrocyclobuta[a]naphthalene [ No CAS ]
  • exo-8b-cyano-1-(2-hydroxyethoxy)-4-hydroxymethyl-1,2,2a,8b-tetrahydrocyclobuta[a]naphthalene [ No CAS ]
  • 60
  • [ 764-48-7 ]
  • [ 1398507-23-7 ]
YieldReaction ConditionsOperation in experiment
100% A solutionof 0.176 g (1.1 mmol) of bromine in 2 mL of chloroform was added dropwise to a stirred mixture of 0.087 g (1.1 mmol) of selenium and 3 mL ofchloroform. After dissolution of selenium, the obtained solution of selenium dibromide was cooled to -20 and added dropwise to a solution of 0.097 g(1.1 mmol) of compound 1 in 5 mL of chloroformcooled to -20 as well. The reaction mixture was warmed to room temperature and stirred for 30 min,0.185 g (2.2 mmol) of NaHCO3 was added, and the mixture was further stirred for 6 h and filtered; the solvent was removed. Yield 0.278 g (100%), colorlessoil. 1H NMR spectrum, delta, ppm: 2.87 d (4H, CH2Se,3J = 4.6 Hz), 3.87 m (4H, CH2O), 3.99-4.02 m (4H,CH2O), 5.12 t (2H, CHO, 3J = 4.6 Hz). 13 NMRspectrum, deltaC, ppm: 29.70 (CH2Se, 1JCSe = 69 Hz),65.32 (CH2O), 104.37 (CHO). 77Se NMR spectrum,deltaSe: 87.5 ppm. Found, %: 38.23; H 5.76; Se 31.49.814O4Se. Calculated, %: C 37.96, H 5.57, Se 31.19.
  • 61
  • [ 764-48-7 ]
  • [ 1378388-20-5 ]
  • C21H20O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate; In water; at 95℃; for 1.5h;Inert atmosphere; Taking compound I (20.03g, 70mmol), 2-ethylene oxy ethanol (9.36g, 108mmol), palladium acetate (0.80g, 3 . 6mmol), 1,3-double-(diphenylphosphine) propane (2.96g, 7.2mmol), potassium carbonate (14.56g, 104mmol) in 200 ml of water and stir the, 95 C reflux reaction 1.5h, the reaction is complete, cooling to room temperature, is added to the reaction solution in the 100 ml ethyl acetate, stirring 5min, slowly dropping 37% concentrated hydrochloric acid 16 ml, then completing, stirring reaction 1h, after the reaction is complete by adding ethyl acetate 200 ml, liquid, the organic layer for 10% potassium carbonate aqueous solution to wash once, the organic layer dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain compound III (19.62g, 96%), adding 67 ml of methanol in 65 C reflow 10min, slow cooling to room temperature 1h, filtering to obtain compound III (18.62g, 91%).
  • 62
  • [ 764-48-7 ]
  • 7-(6-bromonaphthalen-2-yl)-7-azabicyclo[2.2.1]heptane [ No CAS ]
  • 1-(6-(7-azabicyclo[2.2.1]heptan-7-yl)naphthalen-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With palladium diacetate; triethylamine; diphenylphosphinopropane; In ethylene glycol; at 145℃; for 5h;Inert atmosphere; 10098] Compound 2, 1 -(6-(7-azabicyclo[2.2. 1]heptan-7- yl)naphthalen-2-yl)ethanone, was synthesized by the inventors.10099] Specifically, Compound 2c obtained in Example1-3 (184 mg, 0.61 mmol), palladium(II) acetate (Pd(OAc)2,6.8 mg, 0.03 mmol), diphenylphosphinopropane (DPPP,25.2 mg, 0.06 mmol), and ethyleneglycol (1.5 mE) were added to an oven-dried flask with two necks and charged with argon gas. Afier oxygen present in the mixture was removed by adding the argon gas to the mixture, <strong>[764-48-7]ethyleneglycol vinyl ether</strong> (279 pL, 1.53 mmol) and Et3N (255 pL, 1.83 mmol) obtained by distillation were sequentially added thereto. The resulting mixture was stirred at 145 C. for 5 hours using a silicone oil container. The mixture was cooled to room temperature, and stirred with a 6N hydrochloric acid (HC1) aqueous solution (4 mE) at 60 C. for 4 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate (100 mE). An organic layer was washed with water (50 mE), a 5% sodium bicarbonate aqueous solution (50 mE), and a saturated saline solution (50 mE) and dehydrated with anhydrous sodium sulfate (10 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by colunm chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using EtOAc/hexane as a developer), thereby obtaining a yellow solid, Compound 2 (100 mg, 62%). By further purification using recrystallization (using 3% CH2C12/hexane as a solvent), a yellow solid, Compound 2 (32 mg, 20%), was obtained.10100] ?H NMR (CDC13, 300 MHz, 298 K, oe): 8.32 (d, J=1.5 Hz, 1H), 7.93 (dd, J=8.7, 1.8 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.24 (dd, J=8.7, 2.1 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 4.37-4.34 (m, 2H), 2.67 (s, 3H),1.87-1.84 (m, 4H), 1.54-1.5 (m, 4H); ?3C NMR (CDC13, 75 MHz, 298 K, oe): 198.0, 148.6, 137.7, 131.9, 131.0, 130.4, 127.0, 126.7, 124.7, 119.8, 110.3, 58.3, 29.0, 26.7; IR (KBr, cm?): 1670; HRMS: mlz calcd for C,8H,9N0 [M] 265. 1467, C,8H2QNO [MH] 266.1545; found 265.1467 [M],266.1547 [MW]; mp: 118-120 C.
  • 63
  • [ 764-48-7 ]
  • 6-bromo-N-isopropylnaphthalene-2-amine [ No CAS ]
  • 1-(6-(isopropylamino)naphthalen-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With palladium diacetate; triethylamine; diphenylphosphinopropane; In ethylene glycol; at 145℃; for 5h;Inert atmosphere; <2-2> Synthesis of Compound 3 (1-(6-(isopropylamino)naphthalen-2-yl)ethanone) Compound 3, 1-(6-(isopropylamino)naphthalene-2-yl)ethanone, was synthesized by the inventors. Specifically, Compound 3a obtained in Example 2-1 (550 mg, 2.1 mmol), Pd(OAc)2 (23 mg, 0.11 mmol), DPPP (86 mg, 0.22 mmol), and ethyleneglycol (3 mL) were added to an oven-dried flask with two necks and charged with argon gas. Oxygen present in the mixture was removed by adding the argon gas to the mixture, and ethyleneglycolvinylether (1.14 mL, 6.2 mmol) and Et3N obtained by distillation (723 muL, 5.2 mmol) were sequentially added thereto.
  • 64
  • [ 936942-97-1 ]
  • [ 764-48-7 ]
  • (1-(6-morpholinonaphthalen-2-yl)ethanone) [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With palladium diacetate; triethylamine; diphenylphosphinopropane; In ethylene glycol; at 145℃;Inert atmosphere; 10136] Compound 8, 1 -(6-morpholinonaphthalen-2-yl) ethanone, was synthesized by the inventors.10137] Specifically, Compound 8a obtained in Example6-1 (97 mg, 0.33 mmol), Pd(OAc)2 (3.8 mg, 0.017 mmol), DPPP (13.8 mg, 0.034 mmol), and ethylene glycol (1 mE) were added to an oven-dried flask with two necks and charged with argon gas. Oxygen present in the resulting mixture was removed by adding the argon gas to the mixture, and ethyleneglycolvinylether (183 pL, 1.0 mmol) and Et3N (116 pL, 0.84 mmol) obtained by distillation were sequentially added thereto. The mixture was stirred at 145 C. for 4 hours using a silicone oil containet The mixture was cooled to room temperature and stirred with a 6N HC1 aqueous solution (1.5 mE) at 60C. for 4 hours. The mixturewas cooled to room temperature and diluted with ethyl acetate (100 mE). An organic layer was washed with water (3x50 mE) and a saturated saline solution (50 mE) and dehydrated with anhydrous sodium sulfate (10 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by column chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using 1% MeOH/CH2C12 as a developer), thereby obtaining a brown solid, Compound 8 (54 mg, 64%). By further purification using recrystallization (using 1% MeOH/CH2C12 as a solvent), a brown solid, Compound 8 (36 mg, 43%), was obtained.10138] ?H NMR (CDC13, 300 MHz, 298 K, oe): 8.34 (s,1H), 7.97 (d, J=8.7 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H), 7.69 (d,J=8.7 Hz, 1H), 7.26-7.31 (m, 1H), 7.1 (s, 1H), 3.91 (t, J=4.8Hz, 1H), 3.32 (t, J=4.6 Hz, 1H), 2.68 (s, 3H); ?3C NMR(CDC13, 75 MHz, 298 K, oe): 198.0, 151.2, 137.4, 132.4,130.9, 130.2, 127.3, 127.1, 124.9, 119.0, 109.2, 67.0, 49.0,26.7; IR (KBr, cm?): 1666; HRMS: m/z calcd forC,6H,7N02 [M] 255.1259, C,6H,8N02 [MH] 256.1292;found 255.1256 [M], 256.1279 [MW]; mp: 149-151 C.
  • 65
  • [ 764-48-7 ]
  • 4-(6-bromonaphthalene-2-ylamino)cyclohexanol [ No CAS ]
  • 1-(6-(4-hydroxycyclohexylamino)naphthalen-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With palladium diacetate; diphenylphosphinopropane; In ethylene glycol; at 145℃; for 5h;Inert atmosphere; The mixture was stirred at 145 C. for 5 hours using a silicone oil container. The mixture was cooled to room temperature and stirred with a 6N HCl aqueous solution (2 mL) at 60 C. for 4 hours. The mixture was cooled to room temperature and diluted with ethyl acetate (150 mL). An organic layer was washed with water (50 mL), a 5% sodium bicarbonate aqueous solution (50 mL), and a saturated saline solution (50 mL) and dehydrated with anhydrous sodium sulfate (15 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by column chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using 50% EtOAc/CH2Cl2 as a developer), thereby obtaining a bright yellow solid, Compound 5 (203 mg, 72%). By further purification using recrystallization (using 7% CH2Cl2/hexane as a solvent), a bright yellow solid, Compound 5 (120 mg, 42%) was obtained. 1H NMR (CD3CN, 300 MHz, 298 K, delta): 8.33 (s, 1H), 7.84 (dd, J=8.7, 1.8 Hz, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 6.96 (dd, J=9.0, 2.4 Hz, 1H), 6.83 (d, J=1.8 Hz, 1H), 4.84 (d, J=7.8 Hz, 1H), 3.62-3.5 (s, 1H), 3.46-3.34 (m, 1H), 2.71 (d, J=4.5 Hz, 1H), 2.59 (s, 3H), 2.13-2.09 (m, 4H), 1.46-1.2 (m, 4H); 1H NMR (DMSO-d6, 500 MHz, delta): 8.33 (d, J=1 Hz, 1H), 7.77-7.73 (m, 2H), 7.58 (d, J=8.5 Hz, 1H), 7.02 (dd, J=9.0, 2.0 Hz, 1H), 6.76 (d, J=1.5 Hz, 1H), 6.21 (d, J=7.5 Hz, 1H), 4.57 (d, J=4.5 Hz, 1H), 3.49-3.43 (m, 1H), 3.35-3.3 (m, 1H), 2.58 (s, 3H), 2.03-2 (m, 2H), 1.89-1.86 (m, 2H), 1.38-1.31 (m, 2H), 1.27-1.2 (m, 2H); 13C NMR (CDCl3, DMSO-d6, 125 MHz, 300K, delta): 196.8, 148.3, 138.0, 130.4, 129.4, 125.2, 124.6, 124.0, 119.0, 102.0, 68.4, 50.1, 33.9, 30.1, 26.3; IR (KBr, cm-1): 1669; HRMS: m/z calcd for C18H21NO2 [M+] 283.1572, C18H22NO2 [MH+] 284.1651; found 283.1575 [M+], 284.1648 [MH+]; mp: 186-188 C.
  • 66
  • [ 764-48-7 ]
  • [ 180623-98-7 ]
  • 1-(2-amino-3-chloro-5-methylphenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate; In water; toluene; at 90℃; for 24h; A mixture of Int-172-22 (7 g, 26.17 mmol), 23 (14.09 mL, 157 mmol), K2CO3 (4.34 g, 31.4 mmol), DPPP (521 mg, 1.3 mmol) and Pd(OAc)2 (59 mg, 0.26 mmol) in 60 mL H2O/toluene (9:1) was heated at 90oC for 24h. After the mixture was cooled to room temperature, concentrated HCl (15 mL) was slowly added and the mixture was stirred at room temperature for 1h. The product was extracted with EtOAc (3X). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The product was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes) and obtained as a pale yellow solid (1.3 g) in 27% yield. LCMS: (M+1) m/z = 184.
  • 67
  • [ 216393-67-8 ]
  • [ 764-48-7 ]
  • 1-(2-amino-5-chloro-3-fluorophenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate; In water; toluene; at 90℃; for 24h; A mixture of Int-172-27 (5 g , 18.4 mmol), 23 (9.9 mL, 110.5 mmol), K2CO3 (3.05 g, 22.1 mmol), DPPP (366 mg, 0.92 mmol) and Pd(OAc)2 (41 mg, 0.18 mmol) in 60 mL H2O/toluene (9:1) was heated at 90oC for 24h. After the mixture was cooled to room temperature, concentrated HCl (14 mL) was slowly added and the mixture was stirred at room temperature for 1h. The product was extracted with EtOAc (3X). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The product was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes) and obtained as a pale brown solid (1.3 g) in 37% yield. LCMS: (M+1) m/z = 188.
  • 68
  • [ 764-48-7 ]
  • 2-fluoro-6-iodo-4-(trifluoromethoxy)aniline [ No CAS ]
  • 1-(2-amino-3-fluoro-5-(trifluoromethoxy)phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate; In 1,4-dioxane; water; at 90℃; A mixture of Int-172-31 (340 mg, 1.06 mmol), Int-172-23 (0.5 mL, 5.30 mmol), K2CO3 (176 mg, 1.27 mmol), DPPP (22 mg, 0.053 mmol) and Pd(OAc)2 (2.4 mg, 0.0106 mmol) in 1,4-dioxane/H2O (2 mL, 9:1 v/v) was heated at 90 oC overnight. After the mixture was cooled to room temperature, concentrated HCl (1 mL) was slowly added and the mixture was stirred at room temperature for 1h. The product was extracted with EtOAc (3X). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The product was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes) as mobile phase. The product was obtained as a pale yellow solid (128 mg) in 51% yield. LCMS: (M+1) m/z = 238.
  • 69
  • [ 764-48-7 ]
  • 2-amino-3-iodo-5-methylbenzonitrile [ No CAS ]
  • 3-acetyl-2-amino-5-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate; In water; toluene; at 90℃; for 24h; A mixture of Int-172-35 (2 g, 7.75 mmol), Int-172-23 (4.17 mL, 46.5 mmol), K2CO3 (1.28 g, 9.3 mmol), DPPP (154 mg, 0.39 mmol) and Pd(OAc)2 (17 mg, 0.08 mmol) in 40 mL H2O/toluene (9:1) was heated at 90oC for 24h. After the mixture was cooled to room temperature, concentrated HCl (8 mL) was slowly added and the mixture was stirred at room temperature for 1h. The product was extracted with EtOAc (3X). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The product was purified by column chromatography using hexanes/EtOAc (0 to 30% EtOAc in hexanes) and obtained as a pale yellow solid (203 mg) in 15% yield. LCMS: (M+1) m/z = 175.
  • 70
  • [ 1112-39-6 ]
  • [ 764-48-7 ]
  • C10H20O4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% at 100 - 120℃; under 200.0 Torr; for 7.5h; Dimethyldimethoxysilane (KBM22; 48.1 g) and HEVE (70.5 g) were mixed in a four-necked flask, and stirred at 100 to 120 C. under normal pressure for 2 hours while distilling off methanol. The mixture was then stirred for 5.5 hours while distilling methanol at 120 C. and 200 mmHg. Thereafter, the pressure was reduced by vacuum pump at 120 C. for 1.5 hours to remove the remaining HEVE. The results of observation of the 1 H-NMR signal of the product and the results of measurement of LC-MS are as follows, and it was confirmed that the desired compound was obtained (yield: 74.0%).
  • 71
  • [ 1185-55-3 ]
  • [ 764-48-7 ]
  • C13H24O6Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.8% at 80 - 100℃; under 200.0 Torr; for 4.5h; <strong>[1185-55-3]Methyltrimethoxysilan</strong>e (Shin-Etsu Silicone KBM13; 34.1 g) and HEVE (2-hydroxyethyl vinyl ether; 69.7 g) are mixed in a four-necked flask and methanol by-produced at 80 C. under normal pressure The mixture was stirred for 1 hour while being distilled. Then, the mixture was stirred while distilling methanol at 80 C. and 200 mmHg for 1 hour, and further at 100 C. and 200 mmHg for 2.5 hours. Thereafter, the pressure was reduced by vacuum pump at 100 C. for 1 hour to remove the remaining HEVE. The results of observation of the 1 H-NMR signal of the product and the results of measurement of LC-MS are as follows, and it was confirmed that the desired compound (VE-13E) was obtained (yield: 83.8%) ).
  • 72
  • [ 764-48-7 ]
  • [ 363-72-4 ]
  • C10H8F4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% 1. Weigh 5.28 g (0.06 mol) of ethylene glycol monovinyl ether dissolved in 100 mL of DMF, add to a 500 mL round bottom flask, add 2.4 g (60%, 0.06 mol) of sodium hydride, and stir the reaction at room temperature for 40 min.2. Dissolve 10.08 g (0.06 mol) of pentafluorobenzene in 200 ml of DMF into a 500 mL three-necked flask and place in an ice water bath. Transfer the product system in the first step reaction to a constant pressure separatory funnel. The mixture was placed in a three-necked flask, and after completion of the dropwise addition, the reaction was stirred at room temperature for 16 hours.3. After completion of the reaction, transfer to a 250 ml separatory funnel, add water to remove DMF, add petroleum ether (3 * 30 mL) to extract the product, take the upper layer of petroleum ether, and then wash the petroleum ether with water (3 * 30 mL). Transfer to an Erlenmeyer flask and add anhydrous magnesium sulfate to remove water. After standing for 12 hours, the petroleum ether was removed by rotary evaporation at 40 C.4. The obtained product was further purified by distillation at 60 C, 10 mmHg to give a pale yellow liquid, 13 g, yield 92%.
  • 73
  • [ 764-48-7 ]
  • [ 1137725-46-2 ]
  • EGVE-ECT [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;Cooling with ice; To a 50 mL round (0129) bottom flask containing a magnetic stir bar was added ECT (5.0 g, 19.0 mmol, 1.0 equivalent), 4-dimethylaminopyridine (4.64 g, 38.0 mmol, 2 equivalents), N,N dicyclohexylcarbodiimide (4.7 g, 22.8 mmol, 1.2 equivalents, and 28 mL methylene chloride. To the solution was then added ethyleneglycol vinyl ether (4.01 g, 45.5 mmol, 2.4 equivalents). The round bottom flask was then capped with a rubber septa and allowed to react over ice for 1 hour and then at room temperature overnight. The solution was then transferred to a separation funnel and was washed 5 times with saturated sodium bicarbonate solution. The organic phase was then collected, dried over anhydrous sodium sulfate, filtered through a plug of cotton, and then isolated via rotary evaporation. The product was then used for the synthesis of aECT without further purification. To a 10 mL round bottom flask was added ethylene glycol vinyl ether esterified ECT (EGVE-ECT) (0.5 g, 1.5 mmol), HEMA (0.195 g, 1.5 mmol), trifluoroacetic acid (TFA) (50 pL, 653 pmol), and methylene chloride 1.0 mL. The reaction was then sealed with a septa and allowed to react overnight. The product was then isolated via silica gel column chromatography using an eluent consisting of ethyl acetate/hexanes (75:25) with 1 % triethylamine. 1H NMR (500 MHz, benzene-d6, ppm) d = 6.16 (1H, singlet, vinyl), 5.24 (1H, vinyl), 4.52 (1H, quartet, acetal), 4.19 (2H, triplet, ester), 4.08 (2H, triplet, ester), 3.28-3.56 (4H, multiplet, OCH2CHCH3OCH2), 2.79 (2H, quartet, SCH2), 2.0-2.4 (4H, multiplet, C(CH3)(CN)CH2CH2), 1.85 (3H, singlet, vinyl-methyl), 1.32(3H, singlet, C(CN)CH3), 1.13 (3H, doublet, acetal-methyl), and 0.82 (3H, triplet, SCH2CH3) (for the labeled H NMR spectrum see supporting information). C NMR (125 MHz, benzene- d6, ppm) d = 216.9, 170.8, 136.6, 125.1, 118.7, 99.3, 63.9, 63.7, 62.6, 62.3, 33.8, 31.0, 29.5, 24.1, 19.2, 18.1, 12.2.
  • 74
  • [ 764-48-7 ]
  • 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
  • 2-(2,6-dioxo-3-piperidyl)-4-[(Z)-2-(2-hydroxyethoxy)vinyl]isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃; for 12h;Inert atmosphere; To a solution of 4-bromo-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione (1.5 g, 4.45 mmol, Intermediate FT) and 2-vinyloxyethanol (784 mg, 8.90 mmol, CAS764-48-7) in dioxane (100 mL) was added P(t-Bu)3 (1.80 g, 889 umol, 2.09 mL, 10% purity), DIPEA (690 mg, 5.34 mmol, 930 uL) and Pd2(dba)3 (407 mg, 444 umol). The reaction mixture was stirred at rt for 12 hours under N2. On completion, the reaction mixture was poured into sat.NH4Cl (30 mL) and extracted with EA (3×100 mL). The combined organic layers were washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=2:1 to 0:1) to give the title compound (600 mg, 33% yield) as a light yellow solid. LC-MS (ESI+) m/z 345.1 (M+H)+.
  • 75
  • [ 26166-92-7 ]
  • [ 764-48-7 ]
  • 2-(2,6-dioxo-3-piperidyl)-5-[2-(2-hydroxyethoxy)ethyl]isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tris-(dibenzylideneacetone)dipalladium(0); N-Methyldicyclohexylamine; In 1,4-dioxane; at 25℃; for 16h; To a solution of 5-bromo-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione (2.00 g, 5.93 mmol Intermediate GA), 2-vinyloxyethanol (1.05 g, 11.8 mmol) in dioxane (15.0 mL) was added P(t-Bu)3 (2.40 g, 1.19 mmol, 10 wt %), Pd2(dba)3 (543 mg, 593 umol) and N-cyclohexyl-N-methyl-cyclohexanamine (1.51 g, 7.71 mmol), and the mixture was stirred at 25 C. for 16 hrs. On completion, the mixture was concentrated in vacuo. The mixture was purified by silica gel column (EA) to give the title compound (2.00 g, 97% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 11.13 (s, 1H), 7.91 (s, 1H), 7.79-7.76 (m, 1H), 7.72 (s, 1H), 7.71-7.67 (m, 1H), 6.08 (d, J 12.8 Hz, 1H), 5.17-5.10 (m, 1H), 4.91-4.86 (m, 1H), 3.96 (t, J=4.8 Hz, 2H), 3.70-3.63 (m, 2H), 2.95-2.84 (m, 1H), 2.65-2.57 (m, 1H), 2.57-2.53 (m, 1H), 2.11-2.01 (m, 1H).
  • 76
  • [ 764-48-7 ]
  • 3-(5-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-2,6-dione [ No CAS ]
  • 3-[5-[(E)-2-(2-hydroxyethoxy)vinyl]-3-methyl-2-oxobenzimidazol-1-yl]piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; toluene; at 25℃; for 16h; To a solution of 3-(5-bromo-3-methyl-2-oxo-benzimidazol-1-yl)piperidine-2,6-dione (1.00 g, 2.96 mmol, Intermediate HN), 2-vinyloxyethanol (782 mg, 8.88 mmol, CAS764-48-7) in dioxane (25 mL) was added P(t-Bu)3 toluene solution (2.08 mL, 591 umol, 10 wt %), Pd2(dba)3 (542 mg, 591 umol) and DIPEA (497 mg, 3.84 mmol) under N2. The mixture was stirred at 25 C. for 16 hours. On completion, the mixture was concentrated in vacuo. The residue was purified by silica gel column to give the title compound (500 mg, 49% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 11.08 (s, 1H), 7.25-7.19 (m, 1H), 7.19-7.09 (m, 1H), 6.99 (d, J=8.4 Hz, 1H), 6.95-6.90 (m, 1H), 6.35 (d, J=7.2 Hz, 1H), 5.88 (d, J=12.8 Hz, 1H), 5.38-5.29 (m, 1H), 5.25 (d, J=7.2 Hz, 1H), 3.99-3.83 (m, 1H), 3.85 (t, J=5.2 Hz, 1H), 3.69-3.61 (m, 2H), 3.39 (s, 3H), 2.97-2.82 (m, 1H), 2.66-2.58 (m, 1H), 2.53 (d, J=1.6 Hz, 1H), 2.06-1.99 (m, 1H).
  • 77
  • [ 764-48-7 ]
  • 2-(3-bromo-5-methoxypyridin-2-yl)acetonitrile [ No CAS ]
  • 2-(5-methoxy-3-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine; In ethylene glycol; at 140℃; for 0.5h;Inert atmosphere; Into a 25 -mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-(3-bromo-5-methoxypyridin-2-yl)acetonitrile (1 g, 4.4 mmol), 2-(vinyloxy)ethan-1-ol (1.9 g, 21.6 mmol), 1,1'-bis(diphenylphosphino)ferrocene (146 mg, 0.26 mmol), and palladium(II) acetate (30 mg, 0.13 mmol). This was followed by the room temperature addition of ethylene glycol (10 mL) and triethylamine (1.2 mL, 8.9 mmol). The mixture was stirred at 140 C for 30 minutes, then diluted with water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organics were dried over anhydrous sodium sulfate, concentrated, and then purified on a silica gel column eluting with petroleum ether/ethyl acetate (2: 1) to yield 2-(5-methoxy-3-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)acetonitrile (500 mg, 48%).
  • 78
  • [ 764-48-7 ]
  • [ 161454-93-9 ]
  • 1-(2,3-dihydrofuro[2,3-b]pyridin-6-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); triethylamine; In 1,2-dimethoxyethane; at 160℃; for 1h; A mixture of 6-chloro-2,3-dihydrofuro[2,3-b]pyridine (8.6 g, 47.4 mmol), ethylene glycol monovinylether (13 mL, 145 mmol), [1,3- bis(diphenylphosphino)propane]palladium(II) dichloride (1.4 g, 2.4 mmol) and TEA (23 mL, 165 mmol) in ethylene glycol (100 mL) is heated to 160 C for 1 h. The resulting mixture is cooled and concentrated under reduced pressure. An aqueous solution of 5 N HC1 (50 mL) is added to the resulting residue, the mixture is stirred for 10 min, and extracted three times with DCM. The combined organic extracts are concentrated under reduced pressure and the resulting residue is slurried in EtOAc. The resulting mixture is filtered and the filtrate is washed three times with water. The organic phase is dried over MgS04and concentrated under reduced pressure to afford the title compound as brown oil, which slowly solidifies upon standing at RT (7.0 g, 82% yield), suitable for use without additional purification. ES/MS m/z 164 (M+H).
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