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[ CAS No. 586330-18-9 ] {[proInfo.proName]}

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Chemical Structure| 586330-18-9
Chemical Structure| 586330-18-9
Structure of 586330-18-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 586330-18-9 ]

CAS No. :586330-18-9 MDL No. :MFCD11976294
Formula : C12H12IN3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 389.15 Pubchem ID :-
Synonyms :

Safety of [ 586330-18-9 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 586330-18-9 ]

* 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 [ 586330-18-9 ]

[ 586330-18-9 ] Synthesis Path-Downstream   1~40

  • 1
  • 4-((2-(dimethylamino)ethyl)-carbamoyl)phenylboronic acid [ No CAS ]
  • [ 586330-18-9 ]
  • 3-[4-(2-dimethylamino-ethylcarbamoyl)-phenyl]-6-nitro-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 2
  • [ 586330-18-9 ]
  • C12H17BN2O3 [ No CAS ]
  • 6-nitro-3-[3-(piperidin-4-ylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 3
  • [ 586330-18-9 ]
  • C14H21BN2O4 [ No CAS ]
  • 3-[3-(3-morpholin-4-yl-propylcarbamoyl)-phenyl]-6-nitro-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 4
  • [ 70315-70-7 ]
  • [ 24424-99-5 ]
  • [ 586330-18-9 ]
YieldReaction ConditionsOperation in experiment
82% With dmap; triethylamine In methanol; acetonitrile
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; 1.2 Step 2. 3-Iodo-6-nitro-indazole-1-carboxylic acid tert-butyl ester 3-Iodo-6-nitro-1H-indazole (7.01 g, 24.25 mmol), 4-(dimethylamino)pyridine (4.44 g) and 6.34 mL of N,N-diisopropyl ethylamine were dissolved in 500 mL of CH2Cl2 and the mixture was cooled to 0° C. (BOC)2)O (7.94 g) was added to the stirring mixture, and the mixture was allowed to warm to room temperature with stirring for 2 hours at room temperature. The reaction was quenched by addition of 400 mL H2O, and the organic layer was separated, washed with brine, dried over MgSO4, filtered and evaporated under reduced perssure. The residue was chromatographed with silica gel (hexanes/EtOAc 0-80%) to give 7.81 g of 3-Iodo-6-nitro-indazole-1-carboxylic acid tert-butyl ester.
  • 5
  • [ 586330-18-9 ]
  • [ 25487-66-5 ]
  • 3-(3-carboxy-phenyl)-6-nitro-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 6
  • [ 586330-18-9 ]
  • [ 14047-29-1 ]
  • 3-(4-carboxy-phenyl)-6-nitro-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 7
  • [ 586330-18-9 ]
  • (3-(aminocarbonyl)phenyl)boronic acid [ No CAS ]
  • 3-(3-carbamoyl-phenyl)-6-nitro-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 8
  • [ 586330-18-9 ]
  • [ 98-80-6 ]
  • [ 586330-19-0 ]
YieldReaction ConditionsOperation in experiment
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
  • 9
  • [ 586330-18-9 ]
  • N,3-diphenyl-1H-indazol-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: 32 percent / Pd(OAc)2; (S)-BINAP 4: 55 percent / HCl / methanol; diethyl ether
  • 10
  • [ 586330-18-9 ]
  • [ 586330-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2
  • 11
  • [ 586330-18-9 ]
  • (2-methoxy-phenyl)-(3-phenyl-1<i>H</i>-indazol-6-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / methanol; diethyl ether
  • 12
  • [ 586330-18-9 ]
  • (2-chloro-phenyl)-(3-phenyl-1<i>H</i>-indazol-6-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / methanol; diethyl ether
  • 13
  • [ 586330-18-9 ]
  • [ 586330-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: 32 percent / Pd(OAc)2; (S)-BINAP
  • 14
  • [ 586330-18-9 ]
  • 6-amino-3-(4-carboxy-phenyl)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 15
  • [ 586330-18-9 ]
  • 6-amino-3-(3-carboxy-phenyl)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 16
  • [ 586330-18-9 ]
  • 6-amino-3-(3-carbamoyl-phenyl)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 17
  • [ 586330-18-9 ]
  • 3-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / diethyl ether; methanol
  • 18
  • [ 586330-18-9 ]
  • 4-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / diethyl ether; methanol
  • 19
  • [ 586330-18-9 ]
  • 3-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / diethyl ether; methanol
  • 20
  • [ 586330-18-9 ]
  • [ 586330-21-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 21
  • [ 586330-18-9 ]
  • [ 586330-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / PdCl2(dppf) 2: 100 percent / H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 22
  • [ 586330-18-9 ]
  • 6-amino-3-[4-(2-dimethylamino-ethylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 23
  • [ 586330-18-9 ]
  • 3-(3-carboxy-phenyl)-6-(2-chloro-phenylamino)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 24
  • [ 586330-18-9 ]
  • 4-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-<i>N</i>-(2-dimethylamino-ethyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / methanol; diethyl ether
  • 25
  • [ 586330-18-9 ]
  • 3-(4-carboxy-phenyl)-6-(2-chloro-phenylamino)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 26
  • [ 586330-18-9 ]
  • 3-(3-carbamoyl-phenyl)-6-(2-chloro-phenylamino)-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 27
  • [ 586330-18-9 ]
  • 6-amino-3-[3-(piperidin-4-ylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 28
  • [ 586330-18-9 ]
  • 3-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-<i>N</i>-piperidin-4-yl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / diethyl ether; methanol
  • 29
  • [ 586330-18-9 ]
  • 6-amino-3-[3-(3-morpholin-4-yl-propylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PdCl2(dppf) 2: H2 / PtO2
  • 30
  • [ 586330-18-9 ]
  • 6-(2-chloro-phenylamino)-3-[4-(2-dimethylamino-ethylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 31
  • [ 586330-18-9 ]
  • 3-[6-(2-chloro-phenylamino)-1<i>H</i>-indazol-3-yl]-<i>N</i>-(3-morpholin-4-yl-propyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP 4: HCl / diethyl ether; methanol
  • 32
  • [ 586330-18-9 ]
  • 6-(2-chloro-phenylamino)-3-[3-(piperidin-4-ylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 33
  • [ 586330-18-9 ]
  • 6-(2-chloro-phenylamino)-3-[3-(3-morpholin-4-yl-propylcarbamoyl)-phenyl]-indazole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PdCl2(dppf) 2: H2 / PtO2 3: Pd(OAc)2; (S)-BINAP
  • 34
  • [ 7597-18-4 ]
  • [ 586330-18-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / I2; KOH / dimethylformamide 2: 82 percent / DMAP; Et3N / acetonitrile; methanol
  • 35
  • [ 586330-18-9 ]
  • [ 3900-89-8 ]
  • [ 927209-08-3 ]
YieldReaction ConditionsOperation in experiment
With phosphoric acid In toluene at 110℃; for 36h; 1.3 Step 3 3-(2-Chloro-phenyl)-6-nitro-1H-indazole To a solution of 3-Iodo-6-nitro-indazole-1-carboxylic acid tert-butyl ester (5.83 g, 14.98 mmol) in 200 mL toluene was added 2-chlorophenyl boronic acid (4.48 g, 28.46 mmol), K3PO4 (7.82 g), Pd2(dba)3 (41.53 mg) and 2-(dicyclohexylphosphino)-2'-methylbiphenyl) (436.68 mg). The reaction mixture was heated to 110° C. and stirred at this temperature for 36 hours. The reaction mixture was cooled and partitioned between water and EtOAc. The orgaic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to give 8.82 g of crude 3-(2-Chloro-phenyl)-6-nitro-1H-indazole, MS (M+H)=275.
  • 36
  • [ 586330-18-9 ]
  • [ 850568-51-3 ]
  • C26H28N4O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; caesium carbonate In 1,4-dioxane at 80℃; Inert atmosphere;
  • 37
  • [ 70315-70-7 ]
  • [ 34619-03-9 ]
  • [ 586330-18-9 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1h;
  • 38
  • [ 586330-18-9 ]
  • [ 2353-44-8 ]
  • tert-butyl 3-((2,6-dioxopiperidin-3-yl)amino)-6-nitro-1H-indazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; 3.1 Step 1: (1492) Following a general procedure from patent application WO2010007944: 3- aminopiperidine-2,6-dione (1 equiv.), tert-butyl 3-iodo-6-nitro-1H-indazole-1-carboxylate (1 equiv.) and cesium carbonate (2 equiv.) are mixed with dioxane (0.2M). The mixture is purged with N2 for 10 min. Palladium acetate (0.1 equiv.) and XANTPHOS (0.1 equiv.) are added to the mixture and the mixture is heated at 90 °C for 18 hours. The reaction mixture is cooled to ambient temperature and concentrated under vacuum. The residue is diluted with water and extracted with ethyl acetate (thrice). The organic layers are combined, dried over sodium sulfate and concentrated under vacuum. The residue is purified by flash chromatography on a silica gel column to provide tert-butyl 3-((2,6-dioxopiperidin-3-yl)amino)-6-nitro-1H-indazole-1-carboxylate.
  • 39
  • [ 586330-18-9 ]
  • 3-((6-nitro-1H-indazol-3-yl)amino)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 40
  • [ 586330-18-9 ]
  • 3-((6-amino-1H-indazol-3-yl)amino)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 16 h
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