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CAS No. : | 886374-01-2 | MDL No. : | MFCD07375056 |
Formula : | C6H5ClFNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | URXHTRZQQSCUAD-UHFFFAOYSA-N |
M.W : | 161.56 | Pubchem ID : | 46738734 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 35.7 |
TPSA : | 22.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.94 cm/s |
Log Po/w (iLOGP) : | 2.08 |
Log Po/w (XLOGP3) : | 1.89 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 1.6 |
Log Po/w (SILICOS-IT) : | 2.41 |
Consensus Log Po/w : | 2.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.41 |
Solubility : | 0.628 mg/ml ; 0.00389 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.98 |
Solubility : | 1.7 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.04 |
Solubility : | 0.148 mg/ml ; 0.000918 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
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 |
---|---|---|
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; for 21h;Inert atmosphere; | A stirred mixture of <strong>[886374-01-2]5-chloro-3-fluoro-2-methoxypyridine</strong> (0.33 g, 2.0 mmol), bis(pinacolato)diboron (0.58 g, 2.3 mmol), [l,l-bis(diphenylphosphino)- ferrocene]palladium(II) chloride, complex with DCM (0.17 g, 0.21 mmol), and potassium acetate (0.61 g, 6.17 mmol) in dry 1,4-dioxane (8.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to and monitored with LC-MS and TLC. After 21 h, the reaction was cooled to rt then filtered through Celite. The organic solvent was removed under reduced pressure, and the black residue was identified as 3-fluoro-2- methoxy-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)pyridine and used without purification. Mass Spectrum (pos.) m/e: 254.0 (M+H)+. | |
1.01 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; dichloromethane; at 100℃;Inert atmosphere; | Nitrogen gas was purged through a mixture of 5-chloro-3-fluoro-2-methoxy- pyridine (700 mg, 4.33 1 mmol), bis(pinacolato)diboron (1.32 g, 5.198 mmol) and potassium acetate (1.27 g, 12.993 mmol) in 1,4-dioxane (10 mL) for 30 mm. Then, [1,1-bis- (diphenylphosphino)-feffocene]palladium(II)chloride complex with DCM (353 mg, 0.433 mmol) was added. Nitrogen gas purging was continued for another 5 mm. The reaction mixture was heated at 100 C overnight. The reaction was monitored by LCMS. After completion of reaction, the mixture was cooled to RT, then filtered through a celite bed. The organic solvent was removed under reduced pressure and the residue obtained was triturated with pentane. The pentane layer was taken and concentrated to obtain 1.01 g of 3-fluoro-2- methoxypyridine-5-boronic acid pinacol ester which was used as such for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | To a solution of compound 2 (3.6g, 17.56mmol, 1 eq) in Dry THF (20ml_), a solution of nBuLi (1.6M in hexane, 1 .5eq) was added dropwise over 10min at -78C and stirred 30min at the same temp. After, 30min crushed dry ice was added portion wise to the above solution at -78C. Then, the reaction mixture was allowed to warm up to RT over 2h. After 2h, the reaction mixture was cooled to 0C and neutralized by conc.HCI. Then, the reaction mixture was concentrates under reduced pressure to give a crude product. The crude product was dissolved in 5M NaOH solution and washed with ether; the aqueous layer was cooled to 0C and acidified to pH 5-6 by cone. HCI. A precipitate formed. The precipitate was filtered and washed with ether to give compound 3 (2.7g, 75.0%) as a white solid. LCMS: m/z 204.1 (M-1 ) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.89% | With sodium methylate; In methanol; at 65℃; for 2h; | To a solution of compound 1 (1 g, 6.687mmol, 1 eq) in Dry Methanol (5ml_), a solution of 30% NaOMe (1 .8ml_, 10.03mmol, 1.5eq) was added dropwise and the reaction mixture was heated to 65C for 2h (Reaction was monitored by 1 HNMR and LCMS). Then, the reaction mixture was cooled to RT and concentrated under reduced pressure to give a residue. Residue was dissolved in EtOAc and washed with water. The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to give compound 2 (750mg, 69.89%) as colorless liquid; which was sufficiently pure to use for next step. |
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