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CAS No. : | 220844-76-8 | MDL No. : | MFCD11976157 |
Formula : | C11H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NAIDMSQWVCKHQE-UHFFFAOYSA-N |
M.W : | 266.09 | Pubchem ID : | 53419781 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.72 |
TPSA : | 39.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.89 cm/s |
Log Po/w (iLOGP) : | 2.43 |
Log Po/w (XLOGP3) : | 2.86 |
Log Po/w (WLOGP) : | 2.78 |
Log Po/w (MLOGP) : | 2.32 |
Log Po/w (SILICOS-IT) : | 2.96 |
Consensus Log Po/w : | 2.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.65 |
Solubility : | 0.0592 mg/ml ; 0.000222 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.34 |
Solubility : | 0.121 mg/ml ; 0.000455 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.63 |
Solubility : | 0.00622 mg/ml ; 0.0000234 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
55% | With potassium phosphate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1.5h; | 4b) Methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate A mixture of 160 mg (0.60 mmol) of methyl 7-bromo-4-quinolinecarboxylate, 200 mg (0.90 mmol) of <strong>[269409-70-3]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol</strong>, 7 mg (0.03 mmol) of palladium(II)acetate, 16 mg (0.06 mmol) of triphenylphosphine, 450 mg (2.10 mmol) of K3PO4 and 50 uL (3.01 mmol) of H2O in 3 mL of dioxane was stirred at 60 C. for 1.5 hr. EtOAc was added then the organics were washed with H2O and brine then concentrated. The residue was suspended in cold EtOAc and the solids were collected by suction filtration, washed with cold EtOAc and dried to give 92 mg (55%) of methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate as a tan solid. 1H NMR (400 MHz, CDCl3): delta 9.75 (s, 1H), 9.03 (s, 1H), 8.63 (d, J=9 Hz, 1H), 8.25 (d, J=2 Hz, 1H), 8.03 (dd, JA=2 Hz, JB=9 Hz, 1H), 7.87 (s, 1H), 7.72 (d, J=8 Hz, 2H), 6.90 (d, J=8 Hz, 2H), 3.98 (s, 3H). ESI-LCMS m/z 280 (M+H)+. |
55% | With potassium phosphate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1.5h; | A mixture of methyl 7-bromo-4-quinolinecarboxylate 2b (160 mg, 0.60 mmol), <strong>[269409-70-3]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol</strong> 3b (200 mg, 0.90 mmol), palladium(II) acetate (7 mg, 0.03 mmol), triphenylphosphine (16 mg, 0.06 mmol), potassium phosphate (450 mg, 2.10 mmol), and water (50 muL, 3.01 mmol) in dioxane (3 mL) was stirred at 60 C for 1.5 hour. Ethyl acetate was added, and then the organics were washed with water and brine, and then concentrated. The residue was suspended in cold ethyl acetate and the solids were collected by suction filtration, washed with cold ethyl acetate and dried to give methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate 4b (92 mg, 55%) as a tan solid. 1H NMR (400 MHz, CDCl3): delta 9.75 (s, 1H), 9.03 (s, 1H), 8.63 (d, J = 9 Hz, 1H), 8.25 (d, J = 2 Hz, 1H), 8.03 (dd, JA = 2 Hz, JB = 9 Hz, 1H), 7.87 (s, 1H), 7.72 (d, J = 8 Hz, 2H), 6.90 (d, J = 8 Hz, 2H), 3.98 (s, 3H); ESI-LCMS m/z 280 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4a) Methyl 7-bromo-4-quinolinecarboxylate To a solution of 750 mg (2.31 mmol) of dimethyl 7-bromo-2,4-quinolinedicarboxylate in a mixture of 20 mL of EtOH, 10 mL THF and 4 mL of H2O was added 925 mg (23.1 mmol) of NaOH. The mixture was stirred at 50° C. An additional 10 mL of THF and 15 mL of H2O were added after 5 min. After 30 min total at 50° C., the solution was concentrated to volume and the pH was adjusted to 4.0 with 1.0 N HCl (aq) followed by the addition of 100 mL of H2O. The resulting solids were collected by suction filtration, washed with H2O and dried. The solids were then added to 10 mL of diphenyl ether and the mixture stirred at 215° C. for 20 min. Upon cooling, 20 mL of hexanes was added and the resulting solids were collected by suction filtration, washed with hexanes and dried. The solids were then suspended in 20 mL of MeOH and 505 muL (6.90 mmol) of thionyl chloride was added. The mixture was refluxed for 1 hr, then an additional 505 muL (6.90 mmol) of thionyl chloride was added. After an additional 1 hr of refluxing, the solvent was evaporated. The residue was diluted with EtOAc then washed with saturated Na2CO3 (aq) and brine then dried over Na2SO4. Concentration of the solution yielded 320 mg (52percent) of methyl 7-bromo-4-quinolinecarboxylate as a beige solid. 1H NMR (400 MHz, CDCl3): delta 9.01 (d, J=4 Hz, 1H), 8.70 (d, J=9 Hz, 1H), 8.35 (s, 1H), 7.92 (d, J=4 Hz, 1H), 7.75-7.72 (m, 1H), 4.03 (s, 3H). ESI-LCMS m/z 267 (M+H)+. |
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