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[ CAS No. 459133-68-7 ] {[proInfo.proName]}

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Chemical Structure| 459133-68-7
Chemical Structure| 459133-68-7
Structure of 459133-68-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 459133-68-7 ]

CAS No. :459133-68-7 MDL No. :MFCD09056828
Formula : C12H12BrIN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RUXGCTDRNQBDSV-UHFFFAOYSA-N
M.W : 423.04 Pubchem ID :53439660
Synonyms :

Calculated chemistry of [ 459133-68-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 82.35
TPSA : 44.12 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.39
Log Po/w (XLOGP3) : 4.22
Log Po/w (WLOGP) : 4.19
Log Po/w (MLOGP) : 4.04
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 3.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.29
Solubility : 0.00215 mg/ml ; 0.00000509 mol/l
Class : Moderately soluble
Log S (Ali) : -4.86
Solubility : 0.00588 mg/ml ; 0.0000139 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00868 mg/ml ; 0.0000205 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.86

Safety of [ 459133-68-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 459133-68-7 ]

* 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 [ 459133-68-7 ]

[ 459133-68-7 ] Synthesis Path-Downstream   1~27

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YieldReaction ConditionsOperation in experiment
100% With triethylamine;Sonication; General procedure: A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol), ditert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonic irradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extracted with dichloromethane (3 × 30 mL). The combined organic layers were dried with anhydrous sodium sulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100%; m.p.: 93-95 C; IR (KBr) nu (cm-1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) delta(ppm): 8.09 (1H, d, J = 8.5 Hz, H-7); 7.55 (1H, t, J = 7.8 Hz, H-4); 7.46 (1H, d, J = 7.9 Hz, H-6); 7.33 (1H,t, J = 7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR delta (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96;114.56; 102.95; 85.48; 28.18; HRMS calculated for C12H13IN2O2: 344.0022, Found: 344.0016.tert-Butyl 3-iodo-5-nitro-1H-indazole-1-carboxylate (2b). Prepared from 3-iodo-5-nitro-1H-indazole (0.2g, 0.69 mmol), di-tert-butyldicarbonate (0.17 g, 0.78 mmol) and triethylamine (1 mL) to give 0.27 g ofa pale yellow solid. Yield: 100%; m.p.: 144-145 C; IR (KBr) nu (cm-1): 1744 (C=O); 1528 (NO2tert-Butyl 3-iodo-1H-indazole-1-carboxylate (2a). A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol),di-tert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonicirradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extractedwith dichloromethane (3 30 mL). The combined organic layers were dried with anhydrous sodiumsulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100%; m.p.: 93-95 C
77.8% With dmap; triethylamine; In dichloromethane; at 25℃; Step 2 - Synthesis of tert-butyl 5-bromo-3-iodo-lH-indazole-l-carboxylateTo a solution of 5-bromo-3-iodo-lH-indazole (8.0 g, 24.7 mmol), Et3N (3.76 g, 37.2 mmol) and DMAP (151 mg, 1.24 mmol) in dry DCM (70 mL) was allowed to stir at 25 C. Boc20 (5.95 g, 27.3 mmol) was added. The mixture was allowed to stir to at 25 C for overnight. The solvent was removed in vacuo and the resulting residue was purified using column chromatography (PE : EtOAc = 50 : 1) to provide tert-butyl 5-bromo-3-iodo-lH-indazole-l- carboxylate (7.0 g, yield: 77.8 %). 1H-NMR (CDC13, 400 MHz) delta 7.94 (d, / = 8.0 Hz, 1H), 7.58-7.61 (m, 2H), 1.64 (s, 9H). MS (M+H)+: 423 / 425.
77.8% With dmap; triethylamine; In dichloromethane; at 25℃; Step 2 - Synthesis of tert-butyl 5-bromo-3-iodo-lH-indazole-l-carboxylate To a solution of 5-bromo-3-iodo-lH-indazole (8.0 g, 24.7 mmol), Et3N (3.76 g, 37.2 mmol) and DMAP (151 mg, 1.24 mmol) in dry DCM (70 mL) was allowed to stir at 25 C. Boc20 (5.95 g, 27.3 mmol) was added. The mixture was allowed to stir to at 25 C for overnight. The solvent was removed in vacuo and the resulting residue was purified using column chromatography (PE : EtOAc = 50 : 1) to provide tert-butyl 5-bromo-3-iodo-lH-indazole-l- carboxylate (7.0 g, yield: 77.8 %). 1H- MR (CDC13, 400 MHz) delta 7.94 (d, J= 8.0 Hz, 1H), 7.58-7.61 (m, 2H), 1.64 (s, 9H). MS (M+H)+: 423 / 425.
With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; The crude product of 5-bromo-3-iodo-lH-indazole was dissolved in CH2C12 (200 ml) under N2. Et3N (14.00 ml, 100.6 mmol) was added followed by (Boc)20 (10.98 g, 50.3 mmol). The reaction was stirred at room temperature overnight. After completion of the reaction, the mixture was diluted with CH2C12 (150 ml) and washed with sat. NaHC03 (200 ml) and sat. NaCl (200 ml). The organic phase was dried over anhydrous MgS04, and evaporated to dryness. The residue was purified by column (30% EtAOc Hexane) to give tert-butyl 5-bromo- 3-iodo- 1 H-indazole- 1 -carboxylate ( 16.20 g).

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  • 3-(3-dimethylamino-prop-1-ynyl)-5-(3-hydroxy-prp-1-ynyl)-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 5
  • [ 459133-68-7 ]
  • 3-(3-dimethylamino-prop-1-ynyl)-5-phenylethynyl-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]
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  • [ 459133-68-7 ]
  • 3-(3-dimethylamino-prop-1-ynyl)-5-[3-(toluene-4-sulfonylamino)-prop-1-ynyl]-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 7
  • [ 459133-68-7 ]
  • 5-(3-dimethylamino-prop-1-ynyl)-3-[3-(toluene-4-sulfonylamino)-prop-1-ynyl]-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]
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  • [ 24424-99-5 ]
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  • [ 945925-76-8 ]
YieldReaction ConditionsOperation in experiment
Scheme 1 - Step 1:; [ 1 -(tert-Butoxycarbonyl)-5-( { [tert-butyl(dimethyl)silyl]oxy} methyl)- lH-indol-2-yl]boronic acid (1 Og, 23.6mmol, prepared as in Tetrahedron Lett. 2002, 45(15), 2695) and tert-baty 5-bromo-3-iodo-lH- indazole-1-carboxylate (7g, 17.3mmol, prepared as in WO2001029025) were dissolved in DME (126ml). 2N Na2CO3 (49ml) was added and the reaction mixture was stirred for 0.5h. Freshly ptrepared Pd(PPh3)4 (80mg, 0.69mmol) was then added and the mixture heated overnight at 850C. On cooling, the reaction was diluted with brine and extracted with EtOAc (x3), dried (MgSO4) and evaporated in vacuo. The crude material was dissolved in acetonitrile (100ml) and (Boc)2O (5.4g, 24.5mmol) and DMAP (3.Og, 24.5mmol) was added. Reaction stirred for 2h at RT. Solvent removed in vacuo. Reaction mixture was then dissolved in EtOAc and washed with 0. IN HCl and brine, dried and solvent evaporated. Product purified by flash column chromatography (silica gel eluant 10% EtOAc / Hexane to afford Intermediate 1 (1 Ig).
  • 10
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  • [ 53857-57-1 ]
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YieldReaction ConditionsOperation in experiment
To a solution of 5-bromoindazole (10 g, 50.75 mmol) in dimethylformamide (100 mL) was added KOH (10 g, 177.63 mmol). Over a period of 2 hours, iodine (20 g, 78.80 mmol) was added. The mixture was treated with a solution OfNa2S2Os (20 g) in water (200 mL), extracted with ethyl acetate, washed with brine, dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The solid was dissolved in dichloromethane (350 mL) and treated with di-tert-butyl dicarbonate (14.4 g, 65.98 mmol) and dimethylaminopyridine (10 mg, 0.08 mmol). The mixture was stirred for 20 minutes at room temperature and passed directly through a bed of silica gel to afford the title compound. MS (DCI/NH3) m/z 422.9 (M+H)+.
  • 11
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  • [ 98-80-6 ]
  • [ 1093306-79-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene; at 20℃; for 120h; To a solution of Example 6OA (2.1 g, 5 mmol) in toluene (10 mL) was addedPd(PPh3)4 (173 mg, 0.15 mmol), a solution OfNa2CO3 (1.1 g, 10 mmol) in water (5 mL), and a solution of phenyl boronic acid (671 mg, 5.5 mmol) in methanol (3 mL). The mixture was stirred at room temperature for 5 days, quenched with water, extracted with ethyl acetate and <n="77"/>purified by silica gel chromatography eluting with 5% ethyl acetate / hexanes to afford the title compounds as a mixture. 1H NMR (500 MHz, DMSOd6) delta ppm 8.28 (d, J=I .53 Hz, 1 H) 8.12 (d, J=8.85 Hz, 1 H) 7.97 - 8.04 (m, 3 H) 7.80 - 7.86 (m, 2 H) 7.75 (d, J=I .83 Hz, 1 H) 7.54 - 7.63 (m, 3 H) 1.68 (s, 9 H) 1.64 (s, 9 H). MS (ESI+) m/z 373.9 (M+H)+.
  • 12
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  • [ 1093306-80-9 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20℃; for 20h; Example 6OB (1 g, 2.55 mmol), dichlorobis(triphenylphosphine)palladium(II) (89 mg, 0.13 mmol), triethylamine (1.78 mL, 12.75 mmol), trimethylsilyl acetylene (0.432 mL, 3.06 mmol), and CuI (24 mg, 0.13 mmol) were combined in dimethylformamide (10 mL) and stirred at room temperature for 20 hours. The mixture was diluted with ethyl acetate, washed with water, and purified by silica gel chromatography to afford the title compounds. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.10 (d, J=8.85 Hz, 1 H) 8.07 (d, J=8.85 Hz, 1 H) 7.97 (d, J=I.83 Hz, 1 H) 7.84 (s, 1 H) 7.82 (dd, J=8.85, 1.83 Hz, 1 H) 7.71 (dd, J=8.54, 1.53 Hz, 1 H) 1.65 (s, 18 H) 0.33 (d, J=0.92 Hz, 18 H).
  • 13
  • [ 1093306-79-6 ]
  • [ 1066-54-2 ]
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  • [ 1093306-84-3 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20℃; for 20h; Example 6OB (1 g, 2.55 mmol), dichlorobis(triphenylphosphine)palladium(II) (89mg,0.13 mmol), triethylamine (1.78 mL, 12.75 mmol), trimethylsilyl acetylene (0.432 mL, 3.06 mmol), and CuI (24 mg, 0.13 mmol) were combined in dimethylformamide (10 mL) and stirred at room temperature for 20 hours. The mixture was diluted with ethyl acetate and purified by silica gel chromatography to afford the title compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.29 (d, J=1.53 Hz, 1 H) 8.09 - 8.19 (m, 3 H) 7.96 - 8.03 (m, 4 H) 7.83 (dd, J=8.85, 1.83 Hz, 1 H) 7.72 (dd, J=8.85, 1.53 Hz, 1 H) 7.50 - 7.65 (m, 6 H) 1.68 (s, 18 H) 0.26 - 0.27 (m, 9 H)
  • 14
  • [ 1692-15-5 ]
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  • [ 1374353-03-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; To a 500 ml round bottom flask equipped with a magnetic stir bar was added tert-butyl 5 -bromo- 3 -iodo-l H-indazole- 1 -carboxylate (6.00 g, 14.2 mmol), followed by the additions of 4-pyridineboronic acid (1.92 g, 15.6 mmol), PdCl2(dppf) (1.16 g, 1.4 mmol) and K3PO4 (9.03 g, 42.5 mmol). The mixture was dissolved in a mixture of 160 ml of dioxane and 40 ml of H20 and stirred overnight at 80C. Upon completion, the reaction mixture was filtered through celite and washed with water (3 x 100 ml). The organic phase was then dried over anhydrous MgS04j filtered and concentrated to dryness to give a crude product. The crude product was column purified to give 5 -bromo-3-(pyridin-4-yi)-l H-indazole (2.74g) as a de- BOc product.
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  • 5-ethynyI-3-(pyridm-4-yl)-1H-indazole [ No CAS ]
  • [ 1374353-06-6 ]
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  • [ 1765-93-1 ]
  • [ 459133-68-7 ]
  • [ 1426845-42-2 ]
YieldReaction ConditionsOperation in experiment
29% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; toluene; at 100℃;Inert atmosphere; Step 3 - Synthesis of tert-butyl 5-bromo-3-(4-fluorophenyl)-lH-indazole-l-carboxylateTo a degassed solution of tert-butyl 5-bromo-3-iodo-lH-indazole-l-carboxylate (423 mg, 1.0 mmol) and 4-fluorophenylboronic acid (168 mg, 1.2 mmol) in dry ethanol : toluene (1 : 10 mL) was added Pd(dppf)Cl2 (3 mg) and Na2C03(4 mL, 2.0 mmol) under N2. The mixture was heated to 100 C and then stirred overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was washed with EtOAc, brine, dried over Na2S04. After being concentrated in vacuo, the resulting residue was purified using prep-HPLC to provide tert- butyl 5-bromo-3-(4-fluorophenyl)-lH-indazole-l-carboxylate (20 mg, yield: 29%). 1H-NMR (CDCI3, 400 MHz) delta 8.03 (d, / = 8.0 Hz, 1H), 7.99 (d, / = 4.0 Hz, 1H), 7.84-7.88 (m, 2H), 7.56-7.59 (m, 1H), 7.13-7.19 (m, 2H), 1.67 (s, 9H). MS (M+H)+: 391 / 393.
29% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; toluene; at 100℃;Inert atmosphere; Synthesis of tert-butyl 5-bromo-3-(4-fluorophenyl)-lH-indazole-l-carboxylate To a degassed solution of tert-butyl 5-bromo-3-iodo-lH-indazole-l-carboxylate (423 mg, 1.0 mmol) and 4-fluorophenylboronic acid (168 mg, 1.2 mmol) in dry ethanol : toluene (1 : 10 mL) was added Pd(dppf)Cl2 (3 mg) and Na2C03(4 mL, 2.0 mmol) under N2. The mixture was heated to 100 C and then stirred overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was washed with EtOAc, brine, dried over Na2S04. After being concentrated in vacuo, the resulting residue was purified using prep-HPLC to provide tert- butyl 5-bromo-3-(4-fluorophenyl)-lH-indazole-l-carboxylate (20 mg, yield: 29%). 1H- MR (CDC13, 400 MHz) delta 8.03 (d, J= 8.0 Hz, 1H), 7.99 (d, J= 4.0 Hz, 1H), 7.84-7.88 (m, 2H), 7.56-7.59 (m, 1H), 7.13-7.19 (m, 2H), 1.67 (s, 9H). MS (M+H)+: 391 / 393.
  • 24
  • [ 153624-46-5 ]
  • [ 459133-68-7 ]
  • 3,5-bis[4-(propan-2-yloxy)phenyl]-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% To a solution of <strong>[459133-68-7]tert-butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate</strong> (30 mg, 0.O7lmmol) in dioxane (0.5 mL) were added (4-isopropoxyphenyl)boronic acid (25 mg, 0.l4mmol), [1,1?- bis(diphenylphosphino) ferrocene]dichloropalladium(ll) complex with dichloromethane (5.8 mg, 0.0071mmol), potassium carbonate (30 mg, 0.22mmol) and water (0.125 mL). The resulting reaction mixture was degassed with nitrogen for 10 mm, heated to 100C for 10 mm in a microwave reactor, then heated to 120C for additionall5 min.Then, the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in DCM (1 mL) and TFA (0.25 mL) was added dropwise. The reactionmixture was stirred at r.t. for 3 h, thenconcentratedinvacuo. The residue was purified by preparative HPLC to afford 7 mg (26%) of the product as a yellow solid.LC/MS m/z: 387.28 (M+H), 773.52 (2M+H).
  • 25
  • C9H17BO2 [ No CAS ]
  • [ 459133-68-7 ]
  • 5-bromo-3-vinyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 120℃; for 0.666667h;Microwave irradiation; Inert atmosphere; General procedure: Method b: Prepared from tert-butyl 3-iodo-1H-indazole-1-carboxylate (0.2 g, 0.58 mmol), 2 eq. of vinyl boronic acid pinacol ester (0.27 mL, 1.62 mmol), tetrakistriphenylphosphine palladium (52 mg,0.045 mmol), an aqueous solution of sodium carbonate 2N (2 mL) and dioxane (7 mL) using microwavemethod described above to obtain 50 mg of a crystalline plates: Yield: 60%.
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  • [ 459133-68-7 ]
  • [ 1093306-84-3 ]
  • 27
  • [ 950603-39-1 ]
  • [ 459133-68-7 ]
  • tert-butyl 5-bromo-3-[5-(morpholinomethyl)-2-thienyl]indazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 3h; To a solution tert-butyl 5-bromo-3-iodo-indazole-1-carboxylate (200 mg, 472 μmol) in dioxane (2 mL) and water (0.4 mL) were added 4-[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2-thienyl]methyl]morpholine (218 mg, 0.708 mmol), Na2CO3 (150 mg, 1.416 mmol) and PdCl2dppf (50 mg, 61 μmol). The reaction was heated to 100 C for 3h. The reaction mixture was passed through a celite pad. The solution was washed with brine, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 0-50% EtOAc/hexane to afford the title compound (140 mg, Yield 62%).
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