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CAS No. : | 936011-17-5 | MDL No. : | MFCD11856042 |
Formula : | C7H6BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GSHIHNCXBSQCLM-UHFFFAOYSA-N |
M.W : | 216.03 | Pubchem ID : | 70700318 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.82 |
TPSA : | 39.19 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) : | -6.69 cm/s |
Log Po/w (iLOGP) : | 1.86 |
Log Po/w (XLOGP3) : | 1.31 |
Log Po/w (WLOGP) : | 1.67 |
Log Po/w (MLOGP) : | 0.68 |
Log Po/w (SILICOS-IT) : | 2.16 |
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) : | -2.28 |
Solubility : | 1.14 mg/ml ; 0.00529 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.73 |
Solubility : | 3.99 mg/ml ; 0.0185 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.96 |
Solubility : | 0.237 mg/ml ; 0.0011 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
64.3% | Stage #1: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -60℃; for 1 h; Stage #2: at -60℃; for 1 h; |
To a solution of diisopropylamine (22.7 g, 0.22 mol) in THF (0.5L) was cooled to -30°C, and then added n-BuLi (140 mL, 0.22 mol). After addition, the resulting solution was stirred for 0.5 h. The mixture was cooled to -60 °C, Example 60a (35.1 g,0.19 mol) dissolved in THF (200 mL) was added dropwise,maintained the temperature below -60 °C, the resulting solution was stirred for 1 h. DMF (20.4 g 0.28 mol) was added dropwise at -60 °C, the resulting solution was stirred for 1 h .The reaction mixture was quenched by saturated NH4C1 (200 mL) aqueous, and allowed warmed to room temperature .the residue was extracted with EtOAc (200 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product (Example 60b, 26.4 g, yield 64.3percent) as a white solid. i NMR ^OO MHz, CDC13) δ 10.28 (s, 1H), 8.40 (s, 1H), 7.16 (s, 1H), 3.95 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.9 g | at 0℃; for 1 h; | To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 °C. The resulting mixture was stirred for 1 hr at 0 °C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE:EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid. |
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