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[ CAS No. 13097-01-3 ] {[proInfo.proName]}

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Chemical Structure| 13097-01-3
Chemical Structure| 13097-01-3
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Product Details of [ 13097-01-3 ]

CAS No. :13097-01-3 MDL No. :MFCD03233075
Formula : C13H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MXBKCOLSUUYOHT-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :300385
Synonyms :

Calculated chemistry of [ 13097-01-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.53
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 3.21
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 3.6
Consensus Log Po/w : 2.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.74
Solubility : 0.0353 mg/ml ; 0.000182 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0637 mg/ml ; 0.000328 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.43
Solubility : 0.00072 mg/ml ; 0.00000371 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 13097-01-3 ]

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

Application In Synthesis of [ 13097-01-3 ]

* 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 [ 13097-01-3 ]

[ 13097-01-3 ] Synthesis Path-Downstream   1~85

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  • [ 13047-06-8 ]
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  • [ 139215-22-8 ]
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  • [ 144729-18-0 ]
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  • [ 107-13-1 ]
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  • 13
  • [ 105-36-2 ]
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  • [ 61308-29-0 ]
  • 14
  • 1-cyano-3-phenylindazole [ No CAS ]
  • [ 13097-01-3 ]
  • 16
  • [ 2243-79-0 ]
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  • 17
  • [ 5176-12-5 ]
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  • 20
  • [ 13097-01-3 ]
  • 2-oxy-3-phenyl-indazole [ No CAS ]
  • [ 61308-33-6 ]
  • 21
  • phenylmagnesium bromide [ No CAS ]
  • etheric solution [ No CAS ]
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  • [ 1608-42-0 ]
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  • [ 54848-26-9 ]
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  • [ 69629-50-1 ]
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  • [ 96546-38-2 ]
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  • 29
  • <i>N</i>-(2-nitro-benzenesulfonyl)-2-phenyl-acetamidine [ No CAS ]
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  • 31
  • [ 1557-50-2 ]
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  • [ 293758-67-5 ]
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  • [ 183110-88-5 ]
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  • [ 342-24-5 ]
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YieldReaction ConditionsOperation in experiment
67% With pyridine; hydrazine; In water; A. 3-Phenyl-1H-indazole To 2-fluorobenzophenone (1.0 g, 5.0 mmol) was added hydrazine (5 mL) and the reaction was heated to reflux for 3 hours. The reaction was then added to water (100 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were dried with sodium sulfate (Na2SO4) and concentrated to an oil. The subsequent hydrazine adduct was heated with pyridine (20 mL) to 170 C. for 4 days. Pyridine was then removed under vacuum and the resulting oil taken up in water (100 mL) and extracted with ethyl acetate (3*30 mL). The combined ethyl acetate layers were dried (Na2SO4) and concentrated to give the final compound (650 mg, 67% yield). 1H NMR (CDCl3) delta 10.6 (br s, 1H), 8.04-7.99 (m, 2H), 7.56-7.50 (m, 2H), 7.47-7.33 (m, 2H), 7.29-7.19 (m, 3H); ES-MS (m/z) 195 [M+1]+.
67% With pyridine; hydrazine; In water; A. 3-Phenyl-1H-indazole To 2-fluorobenzophenone (1.0 g, 5.0 mmol) was added hydrazine (5 mL) and the reaction was heated to reflux for 3 hours. The reaction was then added to water (100 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were dried with sodium sulfate (Na2SO4) and concentrated to an oil. The subsequent hydrazine adduct was heated with pyridine (20 mL) to 170 C. for 4 days. Pyridine was then removed under vacuum and the resulting oil taken up in water (100 mL) and extracted with ethyl acetate (3*30 mL). The combined ethyl acetate layers were dried (Na2SO4) and concentrated to give the final compound (650 mg, 67% yield). 1H NMR (CDCl3) delta 10.6 (br s, 1H), 8.04-7.99 (m, 2H), 7.56-7.50 (m, 2H), 7.47-7.33 (m, 2H), 7.29-7.19 (m, 3H); ES-MS (m/z) 195 [M+1]+.
  • 35
  • ether-hydrochloric acid [ No CAS ]
  • [ 30533-51-8 ]
  • [ 13097-01-3 ]
  • 1-dimethylaminoethyl-3-phenylindazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; N,N-dimethyl-formamide; toluene; EXAMPLE 1 Dimethylaminoethyl chloride hydrochloride (4.32 g) was dissolved in water (20 ml) and the solution was alkalized by the addition of aqueous sodium hydroxide solution. Then the solution was thoroughly mixed with toluene (30 ml) and the organic layer was dried over sodium sulfate. Separately, <strong>[13097-01-3]3-phenylindazole</strong> (3.88 g) was dissolved in dimethyl formamide (60 ml) and sodium hydride, 50% pure, (1.15 g) was added to the solution, followed by adding dropwise the previously prepared toluene solution. The mixture was heated to 70 C and stirred for 75 min. at that temperature and then poured into ice-water and extracted with chloroform. The extract was washed with water, dried over sodium sulfate and concentrated by evaporation. The residue was treated with ether-hydrochloric acid to form hydrochloride. The product was recrystallized from ethanol-ether to obtain 2.0 g of 1-dimethylaminoethyl-<strong>[13097-01-3]3-phenylindazole</strong> hydrochloride (m.p. 163-165 C). Analysis: Calcd. for C17 H20 N3 Cl: C, 67.65; H, 6.68; N, 13.92 (%) Found: C, 67.36; H, 6.59; N, 13.72 (%)
  • 36
  • [ 13097-01-3 ]
  • [ 57614-39-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; paraformaldehyde; In ethanol; b. <strong>[13097-01-3]<strong>[13097-01-3]3-Phenylindazol</strong>e</strong> (9.71 g), paraformaldehyde (2.25 g) and 5% aqueous sodium hydroxide solution (1 ml) were added to ethanol (40 ml) and the mixture was heated under reflux for 3 hours. After cooling the reaction mixture, the precipitated crystals were recovered by filtration to obtain 8.7 g of 1-hydroxymethyl-<strong>[13097-01-3]3-phenylindazole</strong> having a melting point between 103-105 C after recrystallization from ligroine. Analysis: Calcd. for C14 H12 N2 O: C, 74.98; H, 5.39; N, 12.49 (%) Found: C, 74.92; H, 5.18; N, 12.61 (%)
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  • [ 33334-10-0 ]
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  • [ 78502-71-3 ]
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  • [ 1204771-06-1 ]
YieldReaction ConditionsOperation in experiment
Example 7; 2-{(3-phenyl-1H-indazol-1-yl)methyl}thiazole-4-carboxylic acidSodium hydride (added with 40% mineral oil, 9 mg, manufactured by Kanto Chemical Co., Inc.) was added to a solution of 3-phenyl-1H-indazole (40 mg), which had been synthesized according to the literature (T. Edward, C., et al., Tetrahedron, 1991, 47, 9599-9620), in N,N-dimethylformamide (1 mL, manufactured by Kanto Chemical Co., Inc.) under ice cooling, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, ethyl 2-bromomethylthiazole-4-carboxylate (51 mg) synthesized according to the method of the literature (K. Benno, et al., Leibigs. Ann. Chem., 1981, 4, 623-632) was added thereto, and the mixture was stirred overnight at room temperature. Water (1 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×2 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by PTLC (hexane:ethyl acetate=2:1), to give 7.2 mg of the title compound. LC-MS: HPLC retention time 4.08 minutes, m/z 336 (M+H), condition A-1.
  • 40
  • [ 100367-77-9 ]
  • [ 13097-01-3 ]
  • [ 1204771-00-5 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In 1,3,5-trimethyl-benzene; at 180℃; Example 1; Ethyl 2-(3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylateTo a solution of 3-phenyl-1H-indazole (689 mg) synthesized according to the literature (T. Edward C., et al., Tetrahedron, 1991, 47, 9599-9620) in mesitylene (5 mL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (2.38 g, manufactured by Wako Pure Chemical Industries, Ltd.), (1S,2S)-(+)-N,N-dimethylcyclohexane-1,2-diamine (50 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), copper iodide (34 mg, manufactured by Kanto Chemical Co., Inc.), and <strong>[100367-77-9]ethyl 2-bromo-4-thiazolecarboxylate</strong> (840 mg) synthesized according to the literature (T. R. Kelly, et al., J. Org. Chem., 1996, 61, 4623-4633) were added, and the mixture was heated overnight at 180 C. The reaction solution was cooled to room temperature, and then water (20 mL) was added thereto. Ethyl acetate was extracted (3×20 mL), washed with brine (20 mL), and dried (MgSO4), and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 579 mg of the title compound. LC-MS: HPLC retention time 6.80 minutes, m/z 350 (M+H), condition B-1.
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  • [ 1666-17-7 ]
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  • [ 271-44-3 ]
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  • 47
  • [ 43120-26-9 ]
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  • 48
  • [ 54449-01-3 ]
  • 1-benzyl-3-phenyl-1H-indazole [ No CAS ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
25 mg To a solution of 1H-indazole (24 mg, 0.20 mmol) in DMSO (2 mL) was added NaH (60% in oil, 9 mg, 0.21 mmol). After the mixture was stirred at room temperature for 20 min, benzyl chloride (24 mL, 0.21 mmol) was added, and the resultant mixture was stirred at room temperature for 2 h. The mixture was poured into water and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give the benzylated product as a mixture of 4c and 1e. The crude mixture was subjected to the C-H arylation with iodobenzene under PdCl2/phen/Ag2CO3/K3PO4 catalyst (see Section 4.5). The reaction mixture was passed through a pad of short silica gel (EtOAc) and the filtrate was washed with water, brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give the mixture of 5ca and 3ea. Then to a solution of the crude in DMSO (2 mL) was added KOt-Bu (157 mg, 1.40 mmol) and stirred at room temperature for 3 h under air. The mixture was poured into water, and then extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (hexane/EtOAc=2:1) to give 9 (25 mg, 65% from 1H-indazole) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) delta 10.75 (br s, 1H), 8.08-7.95 (m, 3H), 7.57-7.35 (m, 5H), 7.26-7.19 (m, 1H); 13C NMR (CDCl3, 100 MHz) delta 145.83, 141.66, 133.54, 128.88, 128.15, 127.63, 126.81, 121.40, 121.17, 121.01, 110.06; HRMS calcd for C13H21N2 [M+H]+: 195.0922, found: 195.0923.
  • 49
  • [ 591-50-4 ]
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  • [ 73183-34-3 ]
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  • 50
  • [ 1431708-73-4 ]
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  • 52
  • (E)-2,6-dimethyl-4-(phenyldiazenyl)phenol [ No CAS ]
  • [ 13097-01-3 ]
  • 53
  • [ 1441096-60-1 ]
  • phenylmagnesium halide [ No CAS ]
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  • 55
  • [ 96-32-2 ]
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  • methyl 2-(3-phenyl-1H-indazol-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; at 60℃; General procedure: 3-(3-methoxyphenyl)-1H-indazole (S3, 163 mg, 0.73 mmol) was dissolved in acetone (2.2 mL) and treated with methyl bromoacetate (0.21 mL, 2.2 mmol, 3.0 equiv). Finely powdered potassium carbonate (720 mg, 2.2 mmol, 3.0 equiv) was added in a single portion, and the resulting suspension was stirred overnight at 60 C. The reaction was then cooled to room temperature and filtered through celite with acetone. The clear filtrate was concentrated under reduced pressure to give the crude product as an oil. This material was purified by column chromatography over silica gel (hexanes/ethylacetate: 100/0 to 70/30) to give the probe ML212 as an oil (186 mg, 86%).
General procedure: General Procedure: For synthesis of indazoles method of Servi and Akgun was used and have published the data (8). The 3-arylindazole acetic acids (10a-10i) were prepared from the corresponding 3-arylindazoles (Table 1) using the method of Teixeira et al. A mixture of an indazole (3.0 g, 0.02 mol) and K2CO3 (1.38 g, 0.01 mol) in DMF (15 mL) was stirred at 80 C for 30 minutes, then excess of methyl bromoacetate (BrCH2COOCH3) (5.0 mL, 0.03 mol) was added and the reaction mixture was stirred for twenty four hours at 80 C. Upon cooling, the mixture was acidified with 10% aqueous HCl solution. The aqueous layer was extracted with ethyl acetate and combined organic extract washed with brine and dried over anhydrous MgSO4. After filtration the solvent was removed under vacuum and resulted oil was purified by column chromatography. For hydrolysis indazole esters and excess of aqueous NaOH solution (10 M) was stirred at refluxfor 5 hours. After cooling, the mixture was acidified with 10% aqueous HCl solution and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and solvent was removed under vacuum. The resulting solid was purified by recrystallization from ethyl acetate (Fig. 2). <strong>[13097-01-3]<strong>[13097-01-3]3-Phenylindazol</strong>e</strong>-1-acetic acid (10a)<strong>[13097-01-3]<strong>[13097-01-3]3-Phenylindazol</strong>e</strong>-1-acetic acid (10a) was synthesized from phenyl-1H-indazole (Fig. 1, structure 9a) (1.9 g, 0.01 mol) and methyl bromoacetate (5.0 mL, 0.03 mol). Yield: 1.6 g (82 %), M.p.: 165 C, IR upsilonmax (KBr/cm-1): 3300, 1520, 1568, 1517, 1492, 1414, 692, 1H NMR (400 MHz, CD3OD)delta: 4.87 (2H, s, CH2), 6.72-7.75 (9H, m, Ar-H), 13C NMR (100MHz, CD3OD) delta: 56, 113, 118, 120, 123, 125, 128, 135, 138, 140, 143, 163, MS (EI): m/z: 252 (M, 40%), 211 (15), 183 (5), 167 (5), 119 (3), 93 (40), 65 (39), Analysis for C15H12N2O2: Found %: C (70.79), H (6.36), N (5.12), Calculated: C(70.83), H (6.32), N (5.16).
  • 56
  • [ 290368-00-2 ]
  • [ 98-80-6 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Microwave irradiation; General procedure: <strong>[290368-00-2]ter<strong>[290368-00-2]t-butyl 3-iodo-1H-indazole-1-carboxylate</strong></strong> (S2, 100 mg, 0.29 mmol) was placed in a microwave vial and dissolved in 1,4-dioxane (11.5 mL). 3-Methoxyphenylboronic acid (88 mg, 0.58 mmol, 2.0 equiv) and tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol, 0.06 equiv) were added, and the resulting mixture was sparged thoroughly with nitrogen. An aqueous solution of sodium carbonate (2.0 M, 0.65 mL, 1.3 mmol, 4.5 equiv) was then added. The biphasic mixture was microwaved for 1 hour at a reaction temperature of 120 C. After cooling to room temperature, the reaction was diluted with ethyl acetate (2 mL), and then filtered through a celite pad with additional ethyl acetate. The filtrate was concentrated under reduced pressure to give an oil. The crude material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 30/70) to give the title compound as an oil (58.0 mg, 89%).
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  • [ 66607-27-0 ]
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  • [ 1204771-01-6 ]
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  • [ 15185-37-2 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
72% With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20℃; for 4h;Inert atmosphere; General procedure: To a stirring solution of I2 (1.5 equiv) and triphenylphosphine (1.5 equiv) in dry CH2Cl2 (10 mL) was added imidazole (3.3 equiv) under a N2 atmosphere and the reaction mixture was stirred for 15-20 min until the color of the solution changed from brown yellow to light yellow. Then, oxime (1 equiv) in dry CH2Cl2 was added to the solution and stirring was continued for another 3-4 hours at room temperature. After completion of the reaction (monitored by TLC), the solvent was removed under reduced pressure. The residue was dissolved in ethylacetate and washed with saturated NH4Cl, followed by brine solution. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography with silica gel and a gradient solvent system of CH3OH to CHCl3 yielded the target compound. The compounds were thoroughly characterized by NMR, IR, HRMS (ESI)and melting points.
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  • [ 110-52-1 ]
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  • 1-(4-bromobutyl)-3-phenyl-1H-indazole [ No CAS ]
  • 64
  • iodo-1H-indazole [ No CAS ]
  • [ 98-80-6 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
71% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; water; at 120℃; for 3h;Inert atmosphere; Sealed tube; Microwave irradiation; General procedure: A mixture of 3-iodo-1H-indazole (1.0equiv), ArB(OH)2 or ArB(OR?)2 (1.2equiv), xs base (typically 3-4equiv, Na2CO3, K2CO3, NaHCO3, Cs2CO3 or KF) and palladium catalyst (0.05equiv, Pd(PPh3)4, PdCl2(PPh3)2 or PdCl2(dppf)) in solvents (DME/H2O, DME/H2O/EtOH, PhMe/EtOH/H2O or DMF/H2O) was degassed with Ar and heated sealed in a microwave reactor (110-130C, 1h). The crude material after passing through Celite using MeOH to rinse the pad was purified by preparative HPLC or flash chromatography on SiO2.
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  • [ 446-52-6 ]
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  • 66
  • [ 77-78-1 ]
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  • C15H15N2(1+)*CH3O4S(1-) [ No CAS ]
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  • [ 108-86-1 ]
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  • [ 362-54-9 ]
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  • 69
  • [ 13097-01-3 ]
  • 1,2-dimethyl-3-phenyl-1H-indazol-2-ium perchlorate [ No CAS ]
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  • [ 13097-01-3 ]
  • 1,2-dimethyl-3-phenyl-2,3-dihydro-1H-indazole [ No CAS ]
  • 71
  • 4-methyl-N-(2-(pyridin-2-yl)phenyl)benzenesulfonamide [ No CAS ]
  • [ 13097-01-3 ]
  • 72
  • [ 105941-87-5 ]
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  • 73
  • [ 5606-41-7 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
47.5% With copper diacetate; In dimethyl sulfoxide; at 85℃; for 3h;Inert atmosphere; Glovebox; Schlenk technique; 1a was added to a solution of Cu(OAc)2 (0.38 g, 2.09 mmol) in DMSO. The mixture was heated at 85 C for 3 h, subsequently poured into brine and extracted with EtOAc. The solvent was concentrated in vacuum. After purification by column chromatography (n-hexane/EtOAc 20:1), a yellow solid was obtained in 47.5% yield. 1H NMR (400 MHz, CDCl3, 300 K): delta/ppm=12.06 (s, 1H), 8.05 (t, J=7.4 Hz,3H), 7.57 (t, J=7.2 Hz, 2H), 7.48 (t, J=7.1 Hz, 1H), 7.34 (t,J=7.5 Hz, 1H), 7.25 - 7.15 (m, 2H). 13C NMR (101 MHz, CDCl3, 300 K): delta/ppm=145.71, 141.75, 133.63, 129.01, 128.24, 127.86, 126.79, 121.34, 121.06, 120.98, 110.41. Anal Calc. for C13H10N2: C,80.39: H, 5.19: N, 14.42. Found: C, 80.38: H, 5.20: N, 14.40.
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  • [ 100-58-3 ]
  • [ 1885-29-6 ]
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  • [ 52919-86-5 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
83.6% 4. Deprotection of N-acetyl-1H-indazole To a microwavepressure tube with a magnetic stirring bar was added 0.1 mmol ofacetylhydrazone 8 and 20.0 mg of silica-supportedMnO2 (0.08 equiv). The capped tube was irradiated under CEMstandardconditionsfor 15 minutes. After it was cooled to room temperature, EtOAc was added todissolve the residue. After filtration, the filtrate was evaporated to drynessunder reduced pressure. To the crude product was added 1 mL of MeOH and 0.5 mL of6N HCl. The resulting mixture was heated at reflux for an hour. The reactionmixture was cooled to room temperature andneutralizedwith asolution of saturated Na2CO3. The organic layer wascollected and dried over anhydrous Na2SO4. The dryingagent was removed by filtration and the solvent was removed in vacuum. Afterpurification by medium-pressure columnchromatography, the deprotectedproduct 8 was obtained in a yield of83.6% in two steps.
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  • [ 52919-86-5 ]
  • [ 119-61-9 ]
  • [ 13097-01-3 ]
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  • [ 52919-86-5 ]
  • [ 119-61-9 ]
  • [ 55076-15-8 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
10.9%; 77.3%; 10.9% With silica-supported MnO2; at 150℃; for 0.5h;Microwave irradiation; General procedure: 3. General procedure of theintramolecular amination of acetylhydrazones To a microwavepressure tube with a magnetic stirring bar was added 0.1 mmol ofacetylhydrazone and 20.0 mg of silica-supported MnO2 (0.08 equiv).The capped tube was irradiated under CEM standard conditions (forreaction time and temperature, see Table 1, Table 2, and Table 3). It wascooled to room temperature. EtOAc or a 1:10 (V/V) mixture of MeOH and CH2Cl2was added to dissolve the residue. After filtration, the filtrate wasevaporated to dryness under reduced pressure. The crude product was purified bymedium-pressure column chromatography.
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  • [ 55076-15-8 ]
  • [ 13097-01-3 ]
YieldReaction ConditionsOperation in experiment
63.2%Chromat.; 29.4%Chromat. With silica-supported MnO2; at 150℃; for 0.75h;Microwave irradiation; General procedure: 3. General procedure of theintramolecular amination of acetylhydrazones To a microwavepressure tube with a magnetic stirring bar was added 0.1 mmol ofacetylhydrazone and 20.0 mg of silica-supported MnO2 (0.08 equiv).The capped tube was irradiated under CEM standard conditions (forreaction time and temperature, see Table 1, Table 2, and Table 3). It wascooled to room temperature. EtOAc or a 1:10 (V/V) mixture of MeOH and CH2Cl2was added to dissolve the residue. After filtration, the filtrate wasevaporated to dryness under reduced pressure. The crude product was purified bymedium-pressure column chromatography.
  • 84
  • [ 1003-09-4 ]
  • [ 13097-01-3 ]
  • 3-phenyl-1-(thiophen-2-yl)-1H-indazole [ No CAS ]
  • 85
  • [ 104-92-7 ]
  • [ 13097-01-3 ]
  • [ 1428979-29-6 ]
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