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[ CAS No. 53857-57-1 ] {[proInfo.proName]}

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Chemical Structure| 53857-57-1
Chemical Structure| 53857-57-1
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Product Details of [ 53857-57-1 ]

CAS No. :53857-57-1 MDL No. :MFCD00839493
Formula : C7H5BrN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :STVHMYNPQCLUNJ-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :761929
Synonyms :

Calculated chemistry of [ 53857-57-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.79
TPSA : 28.68 ?2

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) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.117 mg/ml ; 0.000593 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.469 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 53857-57-1 ]

Signal Word:Warning Class:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53857-57-1 ]

* 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 [ 53857-57-1 ]

[ 53857-57-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 53857-57-1 ]
  • [ 74-88-4 ]
  • [ 465529-56-0 ]
  • [ 465529-57-1 ]
YieldReaction ConditionsOperation in experiment
36%; 52% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydride; In tetrahydrofuran; at 20℃; for 3h; The A14-1 (590mg, 2.99mmol) was dissolved in tetrahydrofuran (10mL), was added NaH in the case of an ice bath with stirring (180mg80%, 6.00mmol),After stirring for 30 minutes was added CH3I (468mg, 3.30mmol), stirring was continued for 3 hours, raised to room temperature, water (20 mL), ethyl acetate (20mL × 3)Extraction, the organic phase was washed with saturated brine (50mL × 3), dried over anhydrous sodium sulfate, and spin dry solvent, the residue was purified by column chromatography (petroleum ether: ethyl acetate= 10:1-3:1) to give A14-2 (230mg, 36%) and A14-3 (330mg, 52%).A14-2: off-white solid. 1HNMR (400MHz, DMSO) delta8.33 (s, 1H), 7.96-7.95 (m, 1H), 7.57 (d, J = 9.2Hz,1H), 7.31-7.28 (m, 1H), 4.16 (s, 3H).A14-3: white solid.
29%; 42.5% 5-Bromo-1-methyl-1 H-indazole (ii) and 5-Bromo-2-methyl-2H-indazole (iii)To a solution of 5-bromo-1 H-indazole (0.19 g, 0.94 mmol) in 3 mL THF at 0 0C was added NaH (0.04 g, 1.03 mmol). The reaction solution was stirred at this temperature for 1 hour before methyl iodide (0.09 mL, 1.41 mmol) was added at 0 0C. The reaction was allowed to warm to room temperature slowly and stirred for 2 hours, quenched with water and concentrated in vacuo. The residue was diluted with water and extracted with DCM twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (hexane:EtOAc = 10:1 ) to give the title compound ii (88.7 mg, 42.5 %) and iii (60.9 mg, 29 %) as two white solids, ii: 1H-NMR (400MHz, DMSO- Cf6) delta ppm 8.02 (d, 1 H), 7.99 (d, 1 H), 7.64 (d, 1 H), 7.50 (dd, 1 H), 4.04 (s, 3H). LCMS(method A): [MH]+ = 21 1/213, tR = 5.19 min. iii: 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.33 (s, 1 H), 7.95 (d, 1 H), 7.57 (d, 1 H), 7.30 (dd, 1 H), 4.16 (s, 3H). LCMS (method A): [MH]+ = 21 1/213, tR = 4.95 min.
29%; 42.5% To a solution of 5-bromo-1 H-indazole (0.19 g, 0.94 mmol) in 3 ml_ of THF at 0 QC was added NaH (0.04 g, 1 .03 mmol). The reaction mixture was stirred at this temperature for 1 h before the addition of methyl iodide (0.09 ml_, 1 .41 mmol) at 0 QC. The reaction was allowed to warm to rt slowly and stirred for 2 h, quenched with water and concentrated in vacuo. The residue was diluted with water and extracted with DCM twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude products were purified by flash chromatography (hexane:EtOAc = 10:1 ) to give the title compound ii (88.7 mg, 42.5 %) and iii (60.9 mg, 29 %) as white solid, ii: 1H-NMR (400MHz, DMSO-d6) Dppm 8.02 (d, 1 H), 7.99 (d, 1 H), 7.64 (d, 1 H), 7.50 (dd, 1 H), 4.04 (s, 3H). LCMS (method A): [MH]+ = 21 1/213, tR = 5.19 min. iii: 1H-NMR (400MHz, DMSO-Cf6) deltappm 8.33 (s, 1 H), 7.95 (d, 1 H), 7.57 (d, 1 H),7.30 (dd, 1 H), 4.16 (s, 3H). LCMS (method A): [MH]+ = 21 1/213, tR = 4.95 min.
Scheme 5:F G R Me HI R Et JK R Pr LM R iPr N Sodium hydride (60% in oil, 1.5 g, 37.5 mmol, 1.2 equiv) was added to a solution of 5- bromoindazole F (6 g, 30.6 mmol, 1 equiv) in DMF (60 mL) at RT. After stirring for 30 min, methyl iodide (2.83 mL, 45.9 mmol, 1.5 equiv) was added and the reaction stirred for another 2 h at RT. The reaction was quenched with sat. NaHC03, extracted with EtOAc (lx), dried over MgS04, filtered, and concentrated under reduced pressure to give a mixture of JV-l and N-2 methylated 5-bromoindazoles G and H, which were separated by silica-gel chromatography using 0?30 % EtOAc/hexanes as eluent. The Nl -alkylated regioisomer G elutes first, followed by the N2-methyl regioisomer H. Other N-l -alkylated 5-bromoindazoles (I, , M) were prepared by the same procedure, substituting the appropriate electrophile for methyl iodide (ethyl iodide, i-propyl iodide, n-propyi iodide).
[000842] To a solution of 5-bromo-lH-indazole, 202A, (4.92 g, 25.0 mmol) in THF (300 mL) at 0 C was added NaH (1.10 g, 27.5 mmol). The reaction solution was stirred at this temperature for 1 hour before methyl iodide (5.32 g, 37.5 mmol) was added at 0 C. The reaction was allowed to warm to room temperature slowly, stirred for 2 hours, and quenched with water and concentrated in vacuo. The residue was diluted with water and extracted with dichloromethane (80 mL x 2). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to give Compound 202B and Compound 202C.
[000791j To a solution of Compound 125A (4.92 g, 25.0 mmol) in THF (300 mL) was added NaH (1.10 g, 27.5 mmol) at 0 C. The reaction solution was stirred at this temperature for 1 h before methyl iodide (5.32 g, 37.5 mmol) was added at 0 C. The reaction was allowed to warm to room temperature slowly, stirred for 2 h, and quenched with water and concentrated in vacuo. The residue was diluted with water and extracted with dichloromethane (80 mL x 2). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to give Compound 125B and Compound 125C. For Compound 125B: LC-MS (ESI) mlz: 211 [M+H] ?H-NMR (CDC13, 400 MHz): (5(ppm) 4.06 (s, 3H), 7.26-7.28 (m, 1H), 7.44-7.48 (m, 1H), 7.86-7.87 (m, 1H), 7.91 (s, 1H). For Compound 125C: LC-MS (ESI) mlz: 211 [M+H] ?H-NMR (CDC13, 400 MHz) (5(ppm) 4.20 (s, 3H), 7.3 1-7.34 (m, 1H), 7.56-7.58 (m, 1H), 7.79-7.80 (m,1H), 7.84 (s, 1H).
Sodium hydride (60% in oil, 1.5 g, 37.5 mmol) was added to a solution of 5-bromoindazole D (6 g, 30.6 mmol) in DMF (60 mL) at RT. After stirring for 30 min, methyl iodide (2.83 mL, 45.9 mmol) was added and the reaction stirred for another 2 h at RT. The reaction was quenched with sat. NaHCO3 (aq), extracted with EtOAc (1×), dried over MgSO4, filtered, and concentrated under reduced pressure to give a mixture of N-1 and N-2 methylated 5-bromoindazoles E and F, which were separated by silica-gel chromatography using 0?30% EtOAc/hexanes.

  • 2
  • [ 53857-57-1 ]
  • [ 420-37-1 ]
  • [ 465529-56-0 ]
YieldReaction ConditionsOperation in experiment
70% Preparation 1 Synthesis of 5-bromo-2-methyl-2H-indazole Add at room temperature under nitrogen, trimethyloxonium tetrafluoroborate (229.34 g, 1.52 mol) portion wise to a mixture of 5-bromo-1H-indazole (199.6 g, 1.01 mol) in ethyl acetate (3.04 L, 31.06 mol), stir 2.5 h and filter to give a white solid. Wash the recovered solid twice with ethyl acetate (500 mL) and then add it portion wise to a cooled aqueous solution of 2 M sodium hydroxide (3.80 L, 7.60 mol) in an ice bath. Stir the mixture for 1 h, sonicate for 15 min., filter and wash the recovered solid twice with water (200 mL). Dry the solid overnight under vacuum, slurry in dichloromethane (1 L) and filter. Concentrate the filtrate and purify by silica gel chromatography eluding with dichloromethane to give the title compound as a yellow solid (149.77 g, 70%). MS (m/z): 211, 213 (M+1).
  • 3
  • [ 53857-57-1 ]
  • [ 1211537-09-5 ]
YieldReaction ConditionsOperation in experiment
50% With acetic acid; Selectfluor; In acetonitrile; at 80℃; for 12h; Step-1: Synthesis of 5-bromo-3-fluoro-1H-indazole Into a 500-mL round-bottom flask was placed 5-bromo-1H-indazole (20 g, 101.51 mmol, 1.00 equiv), selectfluor (71.6 g, 2.00 equiv), AcOH (30 mL), and CH3CN (300 mL). The resulting solution was stirred at 80 C. in an oil bath until completion. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3*100 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). The collected fractions were combined and concentrated under vacuum to deliver the title compound in 11 g (50%) as a white solid. LCMS: 215.1 [M+H]+.
33% With acetic acid; Selectfluor; In acetonitrile; at 80℃; for 16h; Into a 5-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 5-bromo-1H-indazole (200 g, 1.0204mol, 1.00 equiv), CH3CN (3.5L), acetic acid (120 mL), and selectfluoro (544 g, 1.5367mol, 1.51 equiv). The resulting solution was stirred at 80oC until completion. The reaction progress was monitored by LCMS. The resulting solution was diluted with 8 L of ethyl acetate and washed with 3x4000 mL of H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:100-15:85). The collected fractions were combined and concentrated under vacuum to deliver the title compound in 72 g (33%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta 12.77 (s, 1H), 8.03-7.90 (m, 1H), 7.59-7.48 (m, 2H). LCMS: 215 [M+H]+.
9 g With Selectfluor; In N,N-dimethyl acetamide; at 60℃; for 18h;Inert atmosphere; Selectfluor (72 g, 203 mmol) was added to a solution of 5-bromo-lH-indazole (20.0 g, 102 mmol) and N,N-dimethylacetamide (500 mL) under N2. The mixture was heated at 60 C for 18 h, allowed to cool to rt, diluted with ethyl acetate ( 1.5 L), and washed with water (150 mL x The organic layer was dried (Na2S04), filtered, concentrated, and purified by silica gel chromatography (1 : 10; ethyl acetate :petroleum ether) to give 10.8 g of an impure product. Repurification by silica gel chromatography (1 :20; ethyl acetate:petroleum ether) gave 9 g of 5-bromo-3-fluoro-1H-indazole as a light yellow solid. 1H NMR (400 MHz; DMSO-d6): delta 12.77 (s 1H), 7.96 (s, 1H), 7.54 (d, IH), 7.48 (d, 1H).
  • 4
  • [ 313545-34-5 ]
  • [ 53857-57-1 ]
  • [ 1613505-02-4 ]
  • 5
  • [ 74-83-9 ]
  • [ 53857-57-1 ]
  • [ 465529-56-0 ]
  • [ 465529-57-1 ]
YieldReaction ConditionsOperation in experiment
69%; 77% General procedure: NaH (6.1 mmol, 1.2 equiv) was slowly added to a solution of 5-bromoindole/indazole (5.1 mmol,1 equiv) in DMF (10 mL) at 0 C. The mixture was stirred at 0 C for 10 min then the alkylhalide (6.1 mmol, 1.2 equiv) was added at the same temperature. The reaction mixture wascontinued to stir at rt for 2 h. When the reaction was complete [TLC (EtOAc/hexane 1:5)], themixture was extracted with EtOAc (2 × 20 mL) and washed with water (2 × 20 mL). The organiclayer was separated, dried over anhydrous Na2SO4 and the solvent removed under reducedpressure. The residue obtained was purified by flash column chromatography [silica gel (230-400 mesh; Merck), EtOAc/hexane 1:5].
  • 6
  • [ 5722-11-2 ]
  • [ 53857-57-1 ]
  • 1-(1H-indazol-5-yl)-2,2-dimethylcyclopropane-1-carbonitrile [ No CAS ]
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