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[ CAS No. 1257535-45-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1257535-45-7
Chemical Structure| 1257535-45-7
Chemical Structure| 1257535-45-7
Structure of 1257535-45-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1257535-45-7 ]

CAS No. :1257535-45-7 MDL No. :MFCD17168273
Formula : C8H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :YQYJCEGYOVYERM-UHFFFAOYSA-N
M.W : 211.06 Pubchem ID :51342000
Synonyms :

Calculated chemistry of [ 1257535-45-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.76
TPSA : 28.68 Ų

Pharmacokinetics

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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0844 mg/ml ; 0.0004 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.29 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0147 mg/ml ; 0.0000697 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 1257535-45-7 ]

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:

Application In Synthesis of [ 1257535-45-7 ]

* 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 [ 1257535-45-7 ]

[ 1257535-45-7 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 1257535-45-7 ]
  • [ 1628348-02-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 1.5 h / 80 °C 2: 1-methyl-pyrrolidin-2-one / 16 h / 130 °C
  • 2
  • [ 1257535-45-7 ]
  • [ 1628347-98-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 1.5 h / 80 °C 2: 1-methyl-pyrrolidin-2-one / 16 h / 130 °C 3: ammonium hydroxide; hydrogen / methanol / 20 °C
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 1.5 h / 80 °C 2: 1-methyl-pyrrolidin-2-one / 16 h / 130 °C 3: ammonium hydroxide; hydrogen / methanol
  • 3
  • [ 1257535-45-7 ]
  • [ 74-88-4 ]
  • [ 1628348-01-5 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In acetonitrile at 80℃; for 1.5h; 5.1 Example 5: (2,6-dimethyl-2H-indazol-7-yl)methanamine Step 1 : Synthesis of 7-bromo-2,6-dimethyl-2H-indazole [0546] To a solution of 7-bromo-6-methyl-lH-indazole (1 equiv.) in acetonitrile, Cs2C03 (1.3 equiv.) and Mel (3 eq.) was added and reaction was heated at 80 oC for 1.5h. On completion, it was cooled and quenched by addition of water. Extraction was carried out using ethyl acetate. Organic layer was dried over Na2S04 and crude compound was column purified to afford the title compound. (Polar isomer confirmed as N-2-M ethyl and non-polar isomer confirmed as N-l -Methyl by NOE experimentation).
  • 4
  • [ 1257535-45-7 ]
  • [ 74-88-4 ]
  • [ 1628348-01-5 ]
  • [ 2090933-06-3 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In acetonitrile at 80℃; for 1.5h; 5.1 Synthesis of 7-bromo-2,6-dimethyl-2H-indazole To a solution of 7-bromo-6-methyl-1H-indazole (1 equiv.) in acetonitrile, Cs2CO3 (1.3 equiv.) and MeI (3 eq.) was added and reaction was heated at 80° C. for 1.5 h. On completion, it was cooled and quenched by addition of water. Extraction was carried out using ethyl acetate. Organic layer was dried over Na2SO4 and crude compound was column purified to afford the title compound. (Polar isomer confirmed as N-2-Methyl and non-polar isomer confirmed as N-1-Methyl by NOE experimentation).
  • 5
  • [ 1190-73-4 ]
  • [ 1257535-45-7 ]
  • [ 2160582-36-3 ]
YieldReaction ConditionsOperation in experiment
48% With lithium hexamethyldisilazane In tetrahydrofuran at 120℃; for 16h; Inert atmosphere;
  • 6
  • [ 1257535-45-7 ]
  • [ 76513-69-4 ]
  • [ 2158302-09-9 ]
  • [ 1956386-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 66% Stage #1: 7-bromo-6-methyl-1H-indazole With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 20℃; for 2h; 238.A Step A: 7-bromo-6-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole: A solution of 7-bromo-6-methyl-lH-indazole (200 mg, 0.948 mmol) in tetrahydrofuran (2 ml, 0.948 mmol) was cooled with stirring in an ice bath. Sodium hydride (45.5 mg, 1.14 mmol) was added portionwise to the mixture and the reaction was stirred at 0°C for lhour. (2- (chloromethoxy)ethyl)trimethylsilane (0.201 ml, 1.14 mmol) was next added and the reaction stirred for 2 hours while warming to room temperature. The mixture was divided between EtOAc (20 mL) and water (10 mL) and the layers separated. The organic layer was washed with water (2 x 10 mL), brine (10 mL), dried over Na2SC"4 and evaporated in vacuo. The product was purified by chromatography on silica gel using 20 to 40% EtOAc/hexanes as eluent to give 7- bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole (46 mg, 14%) along with isomer 7-bromo-6-methyl-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-indazole (214 mg, 66%). ES+APCI MS m/z 341.1 [M]+.
  • 7
  • [ 1257535-45-7 ]
  • [ 2158302-10-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: caesium carbonate; methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 6 h / 70 °C
  • 8
  • [ 1257535-45-7 ]
  • [ 2158302-11-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: caesium carbonate; methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 6 h / 70 °C 3.1: trifluoroacetic acid / neat (no solvent) / 1.5 h / 20 °C
  • 9
  • [ 1257535-45-7 ]
  • [ 2158297-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: caesium carbonate; methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 6 h / 70 °C 3.1: trifluoroacetic acid / neat (no solvent) / 1.5 h / 20 °C 4.1: hydrogen; 5%-palladium/activated carbon / tetrahydrofuran; methanol / 1 h 4.2: 0.02 h / -30 °C
  • 10
  • [ 1373223-13-2 ]
  • [ 1257535-45-7 ]
YieldReaction ConditionsOperation in experiment
69% With hydrazine hydrate In dimethyl sulfoxide at 60 - 130℃; for 18h; [0461] A solution of 3-bromo-2-fluoro-4-methyl-benzaldehyde (9.2 g, 42.4 mmol, 1.0 equiv) and NH2NI2*H2q (42.4 g, 848 mmol, 41.2 mL, 20 equiv) in DMSO (150 mL) was stirred at 60 °C for 2 h and then at 130 °C for 16 h. Subsequently, the solution was cooled to 20 °C and poured into brine (600 mL) and filtered. The white solid was collected, washed with water (100 mL) and dried under reduced pressure to afford 7-bromo-6-methyl-l//-indazole (6.2 g, 29.4 mmol, 69% yield) as a light yellow solid.'H NMR (400 MHz, chloroform-d): d 10.69 (br s, lH), 8.15 (s, 1H), 7.59 (d,./ = 8.0 Hz, 1H), 7.06 (d,./= 8.4 Hz, 1H), 2.55 (s, 3H).
  • 11
  • [ 1257535-45-7 ]
  • [ 2454490-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 1.5 h / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
  • 12
  • [ 1257535-45-7 ]
  • [ 74-88-4 ]
  • [ 2090933-06-3 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate In acetonitrile at 80℃; for 1.5h; [0462] A mixture of 7-bromo-6-methyl-li -indazole (7.9 g, 37.4 mmol, 1.0 equiv) in CH3CN (250 mL), CS2CO3 (15.9 g, 48.7 mmol, 1.3 equiv) and CH3I (15.9 g, 112 mmol, 6.99 mL, 3.0 equiv) was heated at 80 °C for 1.5 hour. Subsequently, the mixture was cooled to room temperature and filtered. The filtrate was concentrated to provide the crude residue. The residue was diluted with water (200 mL) and extracted with ethyl acetate (60 mL x 3). The combined organic layer was washed with brine 200 mL, dried over anh Na2SC>4, filtered and concentrated under reduced. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate, 10:1 to 2:1) to afford 7-bromo-l,6-dimethyl-indazole (4.9 g, 21.8 mmol, 58% yield) as a yellow solid.
52.55 % With caesium carbonate In acetonitrile at 80℃; 17.1 Step 1: 7-Bromo-1,6-dimethyl-1H-indazole 7-Bromo-6-methyl-1H-indazole (1g, 4.74mmol, 1eq) and cesium carbonate (2.01g, 6.16mmol, 1.3eq) were dissolved in acetonitrile (30mL), iodomethane (2.02g, 14.21 g) was added mmol, 3eq), react at 80°C overnight. LCMS monitored the completion of the reaction, the reaction solution was filtered and concentrated, and the residue was purified by column (ethyl acetate/petroleum ether: 0-50%) to obtain 7-bromo-1,6-dimethyl-1H-indazole (560 mg, yield rate 52.55%), white solid.
  • 13
  • [ 59907-13-0 ]
  • 7-bromo-6-methyl-1H-indazole [ No CAS ]
  • 14
  • [ 1257535-45-7 ]
  • [ 73183-34-3 ]
  • [ 2241721-69-5 ]
YieldReaction ConditionsOperation in experiment
60% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate In 1,4-dioxane at 100℃; for 16h;
  • 15
  • [ 142-68-7 ]
  • [ 1257535-45-7 ]
  • [ 2808243-62-9 ]
YieldReaction ConditionsOperation in experiment
96.53 % With toluene-4-sulfonic acid In dichloromethane at 20℃; 19.1 Step 1: 7-Bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 7-Bromo-6-methyl-1H-indazole (1 g, 4.74 mmol, 1 eq) was dissolved in dichloromethane (20 mL), p-toluenesulfonic acid monohydrate (90.13 mg, 4.74 mmol, 0.1 eq) was added and 2,3-Dihydropyran (797.09 mg, 9.48 mmol, 2 eq). The reaction was left overnight at room temperature. The completion of the reaction was monitored by TLC (petroleum ether:ethyl acetate=5:1). The reaction solution was extracted with water and dichloromethane, and the organic phase was washed with brine and dried over anhydrous sodium sulfate. Filtration, concentration of the filtrate, and column purification of the residue (ethyl acetate/petroleum ether: 0-10%) yielded 7-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H - Indazole (1.35 g, yield: 96.53%), white solid.
  • 16
  • [ 1257535-45-7 ]
  • [ 2811713-00-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); ruphos; potassium phosphate / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
  • 17
  • [ 1257535-45-7 ]
  • [ 2811713-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / acetonitrile / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); ruphos; potassium phosphate / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 18
  • [ 1257535-45-7 ]
  • [ 2811652-45-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / acetonitrile / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); ruphos; potassium phosphate / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / acetonitrile; ethyl acetate / 1 h / 20 °C
  • 19
  • [ 1257535-45-7 ]
  • [ 2402778-80-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 100 °C / Inert atmosphere
  • 20
  • [ 1257535-45-7 ]
  • [ 2811713-05-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 100 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); potassium phosphate / toluene; water; ethanol / 0.5 h / 80 °C / Inert atmosphere
  • 21
  • [ 1257535-45-7 ]
  • [ 2811713-06-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 100 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); potassium phosphate / toluene; water; ethanol / 0.5 h / 80 °C / Inert atmosphere
  • 22
  • [ 1257535-45-7 ]
  • [ 2811576-34-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 100 °C / Inert atmosphere 3: methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II); potassium phosphate / toluene; water; ethanol / 0.5 h / 80 °C / Inert atmosphere 5: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / acetonitrile; ethyl acetate / 1 h / 20 °C
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