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CAS No. : | 929203-04-3 | MDL No. : | MFCD11973623 |
Formula : | C17H20BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MMHFCEWVMQXVEV-UHFFFAOYSA-N |
M.W : | 281.16 | Pubchem ID : | 57345859 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.35 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 86.15 |
TPSA : | 31.35 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.56 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.46 |
Log Po/w (WLOGP) : | 3.05 |
Log Po/w (MLOGP) : | 1.89 |
Log Po/w (SILICOS-IT) : | 2.9 |
Consensus Log Po/w : | 2.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.05 |
Solubility : | 0.0248 mg/ml ; 0.0000883 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.8 |
Solubility : | 0.0446 mg/ml ; 0.000158 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -6.14 |
Solubility : | 0.000205 mg/ml ; 0.000000728 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane for 5 h; Inert atmosphere; Reflux | In a flask,Intermediate 2-4 (13g, 56mmol),United pinacolato ester (21.3g, 84mmol),Potassium acetate (20g, 200mmol),Dioxane (300ml) and bistriphenylphosphine palladium dichloride (1g),Under nitrogen was heated to reflux for 5 hours.cool down,concentrate,The crude product was purified by column chromatography to give the product 14.6g,Yield 93percent. |
15.0 g | for 4 h; Inert atmosphere; Reflux | 3-(4-bromophenyl)pyridine 14.0g, bis(pinacolato)diboron 18.3g, 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex 1.5g, potassium acetate 11.8g, cyclopentylmethyl ether(CPME) 100 ml in a flask, under nitrogen atmosphere this mixture was stirred for 4 hours at reflux temperature. The liquid water addition, toluene liquid to room temperature by cooling the reaction. The organic layer is concentrated, activated carbon dissolved in toluene at column chromatography is purified (soln.: toluene), 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (15.0g) is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.9% | With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane; toluene at 20 - 102℃; for 71 h; Inert atmosphere | That is, under nitrogen, to an 1L flask equipped with a stirrer& cooling tube, Pd (dba)2 21.26g (2.19mmol), tricyclo hexylphosphine / toluene 20percent solution 9.23 g (6.57 mmol) and dehydrated dioxane430mL were put and stirred for 30 minutes at a liquid temperature of 20 ~ 23 . To there, potassium acetate 10.8g (110mmol), bis (pinacolato)diboron 20.4g (80.3mmol) and 3- (4-chloro phenyl) pyridine 14.2g (~73.Ommol) were added while rinsing with 20~ 30mL dehydrated dioxane and wasrefluxed for 30 hours at a liquid temperature of 80 . Since the reaction did not show little progress, it was once cooledto 30 .Pd (dba) 2 21.23g (2.14mmol), tricyclo with the addition of hexyl phosphine / toluene 20percent solution 9.19g (6.55mmol) to, for 30 minutes at a liquid temperature of 30 , followed by liquid It was refluxed for 40 hours at temperature 102 .Thiswas then cooled to room temperature and pure water 300 mL was added and stirred,and the reaction solution was extracted with ethyl acetate 400 mL and water dustwas further extracted with ethyl acetate 200mL. The organic layers were combinedand washed twice with saturated brine 300 mL and liquid separated, and driedover sodium sulfate. After removal of sodium sulfate by filtration, it was evaporatedto give an oil 37.2g of orange color. The resulting oil was purified by silicagel column chromatography (silica gel 200 g, ethyl acetate / hexane = 1/3) to obtaina fraction 111.6 g (GC purity 92.7percent) and a fraction 210.4g (GC purity of 70.3percent) whichcompose compound 2 as main component. fraction 1 was further purified by silicagel column purification (silica gel 200 g, ethyl acetate / hexane = 1/3) togive the compound 210.7g (GC purity 94.8percent). fraction 2 was further purified by silicagel column purification (silica gel 150 g, ethyl acetate / hexane = 1/3) toobtain compound 2 was obtained 5.2 g (GC purity 96.5percent). Total yield was 15.9g(GC purity 95percent, 53.9mmol). The yield was 73.9percent. Compound 2 was a yellow oil |
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