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CAS No. : | 623942-84-7 | MDL No. : | MFCD12406110 |
Formula : | C7H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FNRPOELSJDDLSG-UHFFFAOYSA-N |
M.W : | 218.05 | Pubchem ID : | 11769918 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.56 |
TPSA : | 42.35 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) : | -6.92 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 1.0 |
Log Po/w (WLOGP) : | 1.19 |
Log Po/w (MLOGP) : | 0.77 |
Log Po/w (SILICOS-IT) : | 1.85 |
Consensus Log Po/w : | 1.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.09 |
Solubility : | 1.76 mg/ml ; 0.00806 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.48 |
Solubility : | 7.25 mg/ml ; 0.0332 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.84 |
Solubility : | 0.314 mg/ml ; 0.00144 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 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-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 |
---|---|---|
80% | With manganese(IV) oxide In chloroform for 18 h; Heating / reflux | Step F. 3-Bromo-6-methoxy-pyridine-2-carbaldehyde. A mixture of (3-bromo-6-methoxy-pyridin-2-yl)-methanol (3.25 g, 14.9 mmol) and MnO2 (9.07 g, 104 mmol) in CHCl3 (50 mL) was heated at reflux for 18 h. The mixture was filtered while hot and the filtrate was concentrated. The residue was purified (SiO2; 10percent EtOAc/hexanes) to yield the title compound (2.55 g, 80percent). MS (ESI): mass calcd. for C7H6BrNO2, 214.96; m/z found, 218.2 [M+H]+. 1H NMR (CDCl3): 10.13 (s, 1H), 7.80 (d, J=8.7, 1H), 6.83 (d, J=8.7, 1H), 3.99 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 20℃; for 18 h; | Step E. (3-Bromo-6-methoxy-pyridin-2-yl)-methanol. A mixture of acetic acid 3-bromo-6-methoxy-pyridine-2-ylmethyl ester (3.94 g, 15.2 mmol) and 1 M aq. K2CO3 (26.2 mL, 26.2 mmol) in MeOH (30 mL) was stirred at rt for 18 h. The mixture was concentrated, diluted with H2O (15 mL), and extracted with DCM (3*). The combined extracts were washed with H2O, dried, and concentrated to give the title compound (2.97 g, 90percent). MS (ESI): mass calcd. for C7H8BrNO2, 216.97; m/z found, 218.2 [M+H]+. 1H NMR (CDCl3): 7.68 (d, J=8.6, 1H), 6.60 (d, J=8.6, 1H), 4.67 (dd, J=4.7, 0.6, 2H), 4.01 (t, 4.7, 1H), 3.97 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.75 g | Stage #1: With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 24 h; Stage #2: at 120℃; for 3 h; Stage #3: With potassium carbonate In methanol; water at 20℃; for 1 h; |
To a solution of 3-bromo-6-methoxy-2-methylpyridine (CAS No. 126717-59-7) (5.5 g, 27.2 mmol, 1 equivalent) in chloroform (100 mL) was added 65percent mCPBA (10.8 g, 40.8 mmol, 1.5 equivalents) at 0° C. The reaction mixture was warmed up to room temperature and stirred for 24 hours. To the reaction mixture were added an aqueous sodium thiosulfate pentahydrate solution and a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The resulting organic layer was dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (silica gel, 0percent-20percent methanol/ethyl acetate). The resulting compound was stirred in acetic anhydride (20 mL) at 120° C. for 3 hours. To the reaction mixture was added methanol, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution. The organic layers were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (silica gel, 20percent-75percent ethyl acetate/n-heptane). To the resulting compound in methanol (22 mL) was added potassium carbonate (1 M aqueous solution, 10.4 mL) at room temperature. After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with chloroform. The combined organic layers were washed with a saturated aqueous sodium chloride solution. The organic layers were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to afford the title compound (1.75 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.97 (s, 3H), 4.03 (t, J=4.7 Hz, 1H), 4.68 (dd, J=4.7, 0.8 Hz, 2H), 6.57-6.64 (m, 1H), 7.69 (d, J=8.6 Hz, 1H). |
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