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CAS No. : | 717843-51-1 | MDL No. : | MFCD08061305 |
Formula : | C7H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UNWSCHYDURCYOR-UHFFFAOYSA-N |
M.W : | 202.05 | Pubchem ID : | 21952803 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.4 |
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) : | -5.96 cm/s |
Log Po/w (iLOGP) : | 2.28 |
Log Po/w (XLOGP3) : | 2.21 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 2.46 |
Consensus Log Po/w : | 2.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.277 mg/ml ; 0.00137 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.31 |
Solubility : | 0.992 mg/ml ; 0.00491 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.4 |
Solubility : | 0.081 mg/ml ; 0.000401 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
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 silver carbonate In dichloromethane for 144 h; Inert atmosphere | Synthesis of interaiediate V-c : 3 -Bromo-2-methoxy-4-methyl -pyridineA solution of 3-bromo-4-methyl-2-pyridone V-b (2.20 g, 11.7 mmol), in DCM (80 mL) was treated with Mel (7.29 mL, 117 mmol) and Ag2C03 (6.47 g, 23.5 mmol). The flask was stoppered and stirred under argon for 6 days. The mixture was filtered and purified by column chromatography (Si02; 10percent EtOAc in cyclohexane) to afford the desired product V-c as a clear mobile oil (1.83 g, 80percent). 1H NMR (300 MHz, CDC13) δ 7.94 (d, J = 5.0 Hz, 1H), 6.77 (d, J= 5.1 Hz, 1H), 4.00 (s, 3H), 2.39 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | at 75℃; for 72 h; | Step 3: In a sealed tube, NaOMe (25percent in MeOH, 3.1 mL, 13 mmol) was added to a solution of compound 94 (1.8 g, 8.7 mmol) in MeOH (17 mL). The reaction was heated at 75 °C for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated NH4CI and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography over silica gel, which was eluted with heptanes/EtOAc (0-15percent) to afford compound 95 as a clear oil (991 mg, 56percent yield). 1H NMR (400 MHz, DMSO-c/6) δ 8.00 (d, J = 5.0 Hz, 1 H), 6.98 (d, J = 4.8 Hz, 1 H), 3.90 (s, 3 H), 2.35 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 g | With sodium methylate In methanol; N,N-dimethyl-formamide at 100℃; for 12 h; | (2) Synthesis of 3-bromo-2-methoxy-4-methylpyridine 3-bromo-2-chloro-4-methylpyridine (1 g) was added to DMF (5.6 mL). Sodium methoxide (28percent solution in methanol, 4.6 mL) was added to the solution, and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5percent to 30percent) to give the title compound (1.1 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.40 (s, 3H), 4.00 (s, 3H), 6.77 (d, J=5.1 Hz, 1H), 7.94 (d, Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; for 1.5 h; Inert atmosphere; Sealed tube | Synthesis of intermediate V-d: 2-Methoxy-4-methyl-3-(4,4,5,5-tetramethyl-[l,3,2] dioxaborolan-2-yl)-pyridineA dry sealed tube under argon was charged with 3-bromo-2-methoxy-4-methylpyridine V-c (813 mg, 4.02 mmol), bis(pinacolato)diboron (1.12 g, 4.41 mmol), PdCl2(dppf :DCM (146 mg, 0.20 mmol), OAc (1.18 g, 12.0 mmol) and dry DMF (10 mL). After 1.5h at 100°C, the mixture was cooled to room temperature and a further portion of catalyst (75 mg, 0.092 mmol) was added. The tube was sealed and the mixture stirred at 100°C overnight. The mixture was cooled, the solvent evaporated and the mixture taken up in DCM before washing with water. The separated organics were dried (MgS0 ), filtered and evaporated before purification by column chromatography (Si02; 10percent to 20percent) EtOAc in cyclohexane) to afford the intermediate V-d as a mobile yellow oil (2.14g, 51percent). 1H NMR (300 MHz, CDC13) δ 8.00 (d, J = 5.3 Hz, 1H), 6.65 (d, J = 5.3 Hz, 1H), 3.89 (s, 3H), 2.33 (s, 3H), 1.40 (d, J = 11.1 Hz, 12H). |
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