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CAS No. : | 870062-76-3 | MDL No. : | MFCD03411573 |
Formula : | C5H3ClFNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEHUGRIKMHCJLQ-UHFFFAOYSA-N |
M.W : | 147.54 | Pubchem ID : | 40424737 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.23 |
TPSA : | 33.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 1.27 |
Log Po/w (XLOGP3) : | 1.56 |
Log Po/w (WLOGP) : | 2.0 |
Log Po/w (MLOGP) : | 0.85 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 1.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.23 |
Solubility : | 0.867 mg/ml ; 0.00588 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.87 |
Solubility : | 2.01 mg/ml ; 0.0136 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.32 |
Solubility : | 0.7 mg/ml ; 0.00474 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
20% | With triethylamine;copper diacetate; In dichloromethane; for 72h;Molecular sieve; under air; | A mixture of 2-chloro-3-fluoro-5-hydroxypyridine (2.0 gm, 0.0136 mol), <strong>[178752-79-9]3-(N,N-dimethylamino)phenylboronic acid</strong> (2.24 gm, 0.0136 mol), copper(II)acetate (2.7 gm, 0.0136 mmol), triethylamine (3.8 mL, 0.0272 mol) and powdered 4 molecular sieves in dichloromethane (100 mL) was stirred under air for 3 days. The suspension was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica eluting with ethyl acetate:hexane (3:7) to afford [3-(6-Chloro-5-fluoropyridin-3-yloxy)phenyl]-dimethylamine as colourless oil (0.71g, 20%).ES+ 267 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With triethylamine;copper diacetate; In dichloromethane; for 72.0h;Molecular sieve; under air; | A mixture of 2-chloro-3-fluoro-5-hydroxypyridine (0.8 gm, 0.00544 mol), <strong>[659731-18-7]3-(1-pyrrolidinyl)phenyl boronic acid</strong> (1.03 g, 0.00544 mol), copper(II)acetate (1.08 g, 0.00544 mol), triethylamine(1.5 mL, 0.01088 mol) and powdered 4 molecular sieves in dichloromethane (20 mL) was stirred under air for 3 days. The suspension was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica eluting with ethyl acetate:hexane (3:17) to afford 2-chloro-3-fluoro-5-(3-pyrrolidin-1-ylphenoxy)pyridine as a colourless oil (0.41g, 26%).ES+ 293 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; for 72h; | 6.B To a mixture of .6-chloro-5-fluoropyridin-3-ol (2.43 g) , tert-butyl [ (IS) -2-hydroxy-l-methylethyl] carbamate (3.46 g) , triphenylphosphine (6.48 g) and THF (25 mL) was added dropwise a toluene solution (1.9 M, 13.0 mL) of diisopropylazodicarboxylate at room temperature, and the obtained mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography(hexane/ethyl acetate) to give the title compound (2.88 g) . ¾ NMR (300 MHz, DMS0-d6) δ 1.11 (3H, d, J = 6.8 Hz) , 1.37 (9H, s), 3.69-4.19 (3H, m) , 6.92 (1H, d, J = 7.5 Hz), 7.72 (1H, dd, J = 10.5, 2.5 Hz) , 8.04 (1H, d, J = 2.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2.08333h; Radiolysis; | 2-Chloro-3-fiuoro-5-(4-fiuorophenethoxy)pyridine: To a 50 mL round bottom flask equipped with a stir bar was added 6-chloro-5- fluoropyridin-3-ol (250 mg, 1.695 mmol), 2-(4-fluorophenyl)ethan-1-ol (238 mg, 1.695 mmol), triphenylphosphine (533 mg, 2.033 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.395 mL, 2.033 mmol). The solution warmed to a mild reflux, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reaction solution was concentrated in vacuo and the resulting oil was diluted with a mm of acetone, then concentrated onto Celite in vacuo. The resulting powder was subjected to silica gel chromatography(40 g column, 5-40% EtOAc:Hex) to afford the product 2-chloro-3-fluoro-5-(4-fluorophenethoxy)pyridine (443 mg, 1.643 mmol, 97 % yield) as a white solid. ‘H NMR (500 MHz, chloroform-d) 7.93 (d, J=2.5 Hz, 1H), 7.25 (dd, J=8.5,5.4 Hz, 2H), 7.08-7.01 (m, 3H), 4.21 (t, J=6.7 Hz, 2H), 3.11 (t, J=6.8 Hz, 2H). ESIMS(+) m/z = 270 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
409 mg | With cyanomethylenetributyl-phosphorane; In toluene; at 80℃; for 2h; | Toluene (10 mL), the compound (320 mg) obtained in Reference Example 25-1 described later, and cyanomethylene tributylphosphorane (1.33 mL) were added to 6-chloro-5-fluoropyridin-3-ol (250 mg), and the mixture was heated to 80C and was stirred for 2 hours. The solvent was distilled off under reduced pressure, and the obtained residue was purified by NH silica gel column chromatography (n-hexane/ethyl acetate = 7:3 to 1:1). Diethyl ether was added to the obtained crude product, and the precipitated powder was collected by filtration to give the title compound (409 mg) as a colorless powder. 1H NMR (600 MHz, CHLOROFORM-d) delta ppm 1.26 - 1.36 (m, 2 H) 1.79 - 1.95 (m, 2 H) 2.03 - 2.13 (m, 4 H) 2.56 - 2.62 (m, 1 H) 3.05 - 3.15 (m, 1 H) 3.82 - 3.92 (m, 3 H) 4.67 - 4.74 (m, 1 H) 7.05 (dd, J=9.1, 2.5 Hz, 1 H) 7.92 (d, J=2.5 Hz, 1 H). MS ESI/APCI Multi posi: 287 [M+H]+. |
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