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[ CAS No. 1332527-03-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1332527-03-3
Chemical Structure| 1332527-03-3
Chemical Structure| 1332527-03-3
Structure of 1332527-03-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1332527-03-3 ]

CAS No. :1332527-03-3 MDL No. :MFCD27939304
Formula : C14H11BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :IBADFZNPMLMUBA-UHFFFAOYSA-N
M.W : 303.15 Pubchem ID :67447175
Synonyms :

Calculated chemistry of [ 1332527-03-3 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.07
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.26
TPSA : 27.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.15
Log Po/w (XLOGP3) : 4.23
Log Po/w (WLOGP) : 3.8
Log Po/w (MLOGP) : 3.92
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 3.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.87
Solubility : 0.0041 mg/ml ; 0.0000135 mol/l
Class : Moderately soluble
Log S (Ali) : -4.51
Solubility : 0.0094 mg/ml ; 0.000031 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.57
Solubility : 0.000816 mg/ml ; 0.00000269 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 1332527-03-3 ]

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 [ 1332527-03-3 ]

* 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 [ 1332527-03-3 ]

[ 1332527-03-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 177276-41-4 ]
  • [ 1332527-03-3 ]
  • C28H37N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Reflux;
  • 2
  • [ 1332526-99-4 ]
  • [ 74-88-4 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; 73.A Step A: 6-Bromo-3-methoxy-1-phenyl-1H-indazole Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-1-phenyl-1,2-dihydroindazol-3-one (5 g, 17.30 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL), potassium carbonate (3.7 g, 34.91 mmol, 2.00 equiv), CH3I (2.7 g, 19.01 mmol, 1.10 equiv). The resulting solution was stirred for 3 h at 80° C. in an oil bath. The reaction was then quenched by the addition of water (100 mL). The resulting solution was extracted with ethyl acetate (3*150 mL) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:40) to yield 6-bromo-3-methoxy-1-phenyl-1H-indazole as a yellow solid. MS (m/z): 303 [M+H]+; 1HNMR (400 MHz, CDCl3, ppm): δ 4.168-4.183 (3H, d), 7.251-7.682 (7H, m), 7.837-7.839 (1H, d).
  • 3
  • [ 76561-16-5 ]
  • [ 1332527-03-3 ]
  • 4
  • [ 100-63-0 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate
  • 5
  • [ 20776-50-5 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 1.3: pH 7 2.1: hydrogenchloride; sodium nitrite / ethanol; water / 76 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
  • 6
  • [ 1345403-94-2 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / ethanol; water / 76 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
  • 7
  • 6-bromo-3-methoxy-1H-indazole [ No CAS ]
  • [ 108-90-7 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
48.6% With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; 6.3 General procedure: (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%).
  • 8
  • [ 591-50-4 ]
  • 6-bromo-3-methoxy-1H-indazole [ No CAS ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
48.6% With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; 7.3 General procedure: (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%).
  • 9
  • [ 79762-54-2 ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C
  • 10
  • 6-bromo-3-nitro-1H-indazole [ No CAS ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 2: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C
Multi-step reaction with 2 steps 1: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 2: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C
  • 11
  • [ 108-86-1 ]
  • 6-bromo-3-methoxy-1H-indazole [ No CAS ]
  • [ 1332527-03-3 ]
YieldReaction ConditionsOperation in experiment
66.18% With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; 1.3; 2.3; 3.3; 4.3; 5.3; 8.3; 9.3; 10.3; 11.3; 12.3 (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%).
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