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[ CAS No. 220844-76-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 220844-76-8
Chemical Structure| 220844-76-8
Chemical Structure| 220844-76-8
Structure of 220844-76-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 220844-76-8 ]

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 :

Calculated chemistry of [ 220844-76-8 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.62

Safety of [ 220844-76-8 ]

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:

Application In Synthesis of [ 220844-76-8 ]

* 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.

  • Downstream synthetic route of [ 220844-76-8 ]

[ 220844-76-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 220844-76-8 ]
  • [ 269409-70-3 ]
  • [ 1020568-29-9 ]
YieldReaction ConditionsOperation 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).
  • 2
  • [ 67-56-1 ]
  • [ 31009-04-8 ]
  • [ 220844-76-8 ]
YieldReaction ConditionsOperation 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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