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CAS No. : | 321601-48-3 | MDL No. : | MFCD12828055 |
Formula : | C7H6BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 232.03 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.24 |
TPSA : | 59.42 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) : | -6.11 cm/s |
Log Po/w (iLOGP) : | 2.16 |
Log Po/w (XLOGP3) : | 2.26 |
Log Po/w (WLOGP) : | 1.34 |
Log Po/w (MLOGP) : | 0.51 |
Log Po/w (SILICOS-IT) : | 1.41 |
Consensus Log Po/w : | 1.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.94 |
Solubility : | 0.266 mg/ml ; 0.00115 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.14 |
Solubility : | 0.166 mg/ml ; 0.000717 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.39 |
Solubility : | 0.954 mg/ml ; 0.00411 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
90% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3 h; | A mixture of methyl 6-bromo-3-hydroxypicolinate (4 g, 17.2 mmol), CH3I (7.15 g, 34.5 mmol) and K2C03 (4.76 g, 34.5 mmol) in DMF (50 mL) was stirred at RT for 3 hours. After concentrated, the mixture was diluted with H20 and extracted with EtOAc (50 mL * 3). The organic layer was dried over Na2S04 and concentrated to give crude methyl 6-bromo-3- methoxypicolinate (4 g, yield: 90percent). 1H- MR (CDC13 , 400 MHz) δ 7.56 (d, J= 8.0 Hz, 1H), 7.25 (d, J= 8.0 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 256 / 258. |
78% | With potassium carbonate In acetone for 3 h; Reflux | [0183] Methyl 6-bromo-3-hydroxypicolinate (5.07 g, 21.85 mmol) was dissolved in acetone (75 mL). To the resulting solution were added dropwise potassium carbonate (K2CO3) (4.83 g, 34.96 mmol) and iodomethane (CH3I) (1.77 mL, 28.41 mmol) and the solution was refluxed with heat for 3 hrs. The solution was evaporated under reduced pressure to concentrate, diluted with EtOAc, and washed with water. The washed organic solvent was dried over anhydrous magnesium sulfate (MgSO4) to concentrate. The resulting residue was isolated and purified by silica gel column chromatography (hexane/ethylacetate = 3/1) to give the white title compound (4.18 g, 78 percent). 1H NMR (600 MHz, CDCl3) δ 7.57 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 3.95 (s, 3H), 3.92 (s, 3H). |
76% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4 h; | (step 3 ); A solution of the compound obtained in step 2 (9.42 g) , methyl iodide (2.78 mL) and potassium carbonate (7.29 g) in DMF (80 mL) was stirred at room temperature for 4 hrs, and poured into cold water. The mixture was extracted twice with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 20-25percent ethyl acetate/hexane) and <n="86"/>crystallized from ethyl acetate/hexane to give methyl 6-bromo-3-methoxypyridine-2-carboxylate (7.57 g, 76percent) as white crystals, |
42% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; | A mixture of methyl 6-bromo-3-hydroxypicolinate (10.0 g, 43.10 mmol), Mel (12.3 g, 86.66 mmol) and K2C03 (12.0 g, 86.83 mmol) in DMF (100 mL) was stirred at RT overnight. Then the reaction mixture was concentrated, diluted with water and extracted with EtOAc. The organic layer was dried over a2S04 and concentrated to give methyl 6-bromo-3- methoxypicolinate (4.5 g, yield 42percent). XH-NMR (CDC13, 400 MHz) δ 7.55 (d, J = 8.8 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 246 / 248. |
42% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; | A mixture of methyl 6-bromo-3-hydroxypicolinate (10.0 g, 43.10 mmol), Mel (12.3 g, 86.66 mmol) and K2C03 (12.0 g, 86.83 mmol) in DMF (100 mL) was stirred at RT overnight. Then the reaction mixture was concentrated, diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give methyl 6-bromo-3-methoxypicolinate (4.5 g,yield 42percent). ‘H-NMR (CDC13, 400 MHz) 7.55 (d, J = 8.8 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H), 3.94(s, 3H), 3.90 (s, 3H). MS (M+H): 246 / 248. |
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