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CAS No. : | 1227502-35-3 | MDL No. : | MFCD16607011 |
Formula : | C6H6BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGSDHARUPWHNQU-UHFFFAOYSA-N |
M.W : | 204.02 | Pubchem ID : | 90235329 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.89 |
TPSA : | 53.09 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.34 cm/s |
Log Po/w (iLOGP) : | 1.15 |
Log Po/w (XLOGP3) : | 0.29 |
Log Po/w (WLOGP) : | 0.48 |
Log Po/w (MLOGP) : | 0.5 |
Log Po/w (SILICOS-IT) : | 2.03 |
Consensus Log Po/w : | 0.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.67 |
Solubility : | 4.41 mg/ml ; 0.0216 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.97 |
Solubility : | 22.0 mg/ml ; 0.108 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.62 |
Solubility : | 0.489 mg/ml ; 0.0024 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.63 |
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 |
---|---|---|
15% | With triethylamine; In dichloromethane; at 0 - 20℃; for 17.0h;Inert atmosphere; | Step 3: [0901] To a suspension of <strong>[1227502-35-3]5-bromo-3-(hydroxymethyl)pyridin-2(1H)-one</strong> 62 (350 mg, 1.72 mmol), Et3N (0.71 mL, 5.16 mmol) and CH2Cl2 (15 mL) was slowly added methanesulfonyl chloride (0.27 mL, 3.43 mmol) at 0 C. under nitrogen. The reaction mixture was allowed to warm to room temperature for 17 h and then water was added. The layers were separated and the aqueous was extracted with CH2Cl2. The organic phase was dried over sodium sulfate and filtered. The solvent was removed and the residue was purified by silica gel chromatography (eluting with 0 to 30% ethyl acetate in hexanes) to provide compound 63 (75 mg, 15%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 2.5h;Inert atmosphere; | Step 2: [0899] To a mixture of LiAlH4 (300 mg, 7.93 mmol) and THF (40 mL) at 0 C. under nitrogen was slowly added a solution of ethyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate 61 (1.5 g, 6.09 mmol) and THF (20 mL). After 2.5 hours, the reaction was quenched by slow addition of water. The resultant solid was removed by filtration and the filtrate was extracted with CH2Cl2 (2×100 mL). The combined extracts were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to provide compound 62 (380 mg, 28%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.7% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 20.0h; | 5-bromo-3-(hydroxymethyl)pyridin-2(lH)-one (34.1 mg, 0.167 mmol) was stirred with iodomethane (30.5 mu, 0.201 mmol) and potassium carbonate (115 mg, 0.836 mmol) in DMF (557 mu) in a 2-dram vial containing a Teflon-coated stir bar at room temperature for 1 h. Additional DMF (1.0 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 19 h. The reaction mixture was partitioned between water and ethyl acetate (~4 mL total volume), and the aqueous phase was extracted with ethyl acetate (3x2.5 mL). The combined organic phases were extracted with brine (2x2 mL), then dried over sodium sulfate and filtered. Excess solvent was evaporated from the filtered organic phase to afford 5-bromo-3-(hydroxymethyl)-l- methylpyridin-2(lH)-one (17.7 mg, 0.073 mmol, 43.7% yield) as a clear, pale yellow oil. LCMS MH+: 217.9. HPLC Ret. Time 0.51 min. Method Bl . NMR (400 MHz, CHLOROFORM-d) delta 7.42 (s, 2H), 4.57 (d, J=6.2 Hz, 2H), 3.56 (s, 3H), 3.41 (t, J=6.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.8% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2.5h; | Methyl 5-bromo-2-oxo-l,2-dihydropyridine-3-carboxylate (Combi-Blocks, CAS: 120034-05-1, 0.100 g, 0.431 mmol) was dissolved in THF (4.31 mL) and added dropwise to a 0 C solution of lithium aluminum hydride (0.082 g, 2.155 mmol) in THF (4.31 mL). The reaction mixture was stirred at 0 C for 30 min, then allowed to warm to room temperature and stirred for 2.5 h. Saturated aqueous NH4CI solution (8 mL) was slowly added to the reaction mixture, followed by ethyl acetate (8 mL). The phases were separated, the aqueous phase was extracted with additional ethyl acetate (2x10 mL). The combined organic phases were dried over sodium sulfate and filtered, and excess solvent was evaporated off to afford 5-bromo-3-(hydroxymethyl)pyridin-2(lH)-one (34.1 mg, 0.159 mmol, 36.8% yield) as a white solid. LCMS MH+: 203.9. HPLC Ret. Time 0.47 min. Method Bl . NMR (400 MHz, METHANOLS) delta 7.67 (dt, J=2.7, 1.4 Hz, 1H), 7.51 (d, J=2.7 Hz, 1H), 4.49 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With borane-THF In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; | 4.2.55-Bromo-3-(hydroxymethyl)pyridin-2-ol (7) 5-Bromo-2-hydroxynicotinic acid (6) (2.00 g, 9.17 mmol) wassuspended in dry THF (100 mL). The suspension was cooled to 0 °C and 1M BH3/THF (36.7 mL, 36.7 mmol)was added. The mixturewasstirred at room temperature under argon for 18 h. To the mixture10% HCl was added (pH 1) and the resulting mixture was refluxedfor 1 h. The volatiles were evaporated. The crude was purified by reversed phase column chromatography (sorbent C-18 modified silica gel, eluent MeCN/H2O gradient) to yield 7 (0.993 g, 53%) as awhite solid. 1H NMR (300 MHz, DMSO-d6, d): 4.26-4.29 (m, 2H),7.41-7.44 (m, 1H), 7.52-7.55 (m, 1H), 11.82 (br s, 1H). |
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