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[ CAS No. 1228392-59-3 ] {[proInfo.proName]}

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Chemical Structure| 1228392-59-3
Chemical Structure| 1228392-59-3
Structure of 1228392-59-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1228392-59-3 ]

CAS No. :1228392-59-3 MDL No. :MFCD31560548
Formula : C16H21BrN2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :CPVNSGCXUGJJOL-UHFFFAOYSA-N
M.W : 417.25 Pubchem ID :118029324
Synonyms :

Safety of [ 1228392-59-3 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1228392-59-3 ]

* 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 [ 1228392-59-3 ]

[ 1228392-59-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1228392-59-3 ]
  • [ 327046-79-7 ]
YieldReaction ConditionsOperation in experiment
82.8% With potassium carbonate In acetonitrile at 35℃; for 1.5h; 1.2 Tert-butyl (4-bromo-2-nitrophenyl)carbamate Tert-butyl N-(4-bromo-2-nitro-phenyl)-N-tert-butoxycarbonyl-carbamate 1b (7.12 g, 17.1 mmol) and potassium carbonate (7.08 g, 51.2 mmol) were dissolved in 140 mL of acetonitrile, the solution was heated to 35 °C and reacted for 1.5 hours. The reaction solution was filtered, the filtrate was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: A system) to obtain tert-butyl (4-bromo-2-nitrophenyl)carbamate 1c (4.49 g, bright yellow solid), yield: 82.8%. MS m/z (ESI): 216.8 [M+1-100]
With sodium hydroxide; water In tetrahydrofuran at 65℃; for 22h; 1a.1 Example Ia; (R)-N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-((3-(dimethylamino)pyrrolidin-l- yl)methyl)benzamide (9); Scheme 1; Step 1. tert-Butyi 4-bromo-2-nitrophenylcarbamate (2); [0675] To a solution of 4-bromo-2-nitroaniline 1 (10.0 g; 46.1 mmol) and Boc-anhydride (20.11 g, 92.2 mmol) in THF (100 mL) stirred at room temperature was added a catalytic amount of 4-(dimethylamino)pyridine (DMAP). The reaction mixture was allowed to stir for 90 min, the solvent was removed in vacuo and the residue was dried under vacuum to produce colorless oil. The oil was dissolved in THF (46 mL), treated with an aqueous sodium hydroxide solution (2N, 46 mL) and heated to 65 0C for 18 h. Solid sodium hydroxide (1.8 g, 46.1 mmol) was added to the reaction mixture and heating was continued for 4 h; then the THF was removed in vacuo and a yellow solid crashed from the aqueous solution. The solid was filtered, washed with H2O and dried under vacuum to afford title compound 2 (15 g, >99% yield).[0676] 1H NMR (DMSO-de) δ (ppm): 9.67 (s, IH), 8.05 (d, J= 2.2 Hz, IH), 7.78 (dd, J= 8.8, 2.2 Hz, IH), 7.57 (d, J= 8.8 Hz, IH), 1.43 (s, 9H).
With sodium hydroxide; water In tetrahydrofuran at 70℃; for 22h; 6.a.3 To a stirring solution of 4-bromo-2-nitroaniline 57 (10.0 g, 46.1 mmol) and di- tert-butyl dicarbonate (20.11 g, 92.2 mmol) in THF (100 mL) was added a catalytic amount of DMAP and the reaction mixture was allowed to stir at room temperature for 18 h. The solvent was removed then the crude di-Boc intermediate (MS: 439/441 (M+Na))was placed under vacuum then taken up in THF (46 mL). To this was added a solution of 2N NaOH (46 mL) and the reaction mixture was heated to 7O0C for 4 h. Solid NaOH (1.8 g) was added and the solution was further heated for 18 h then solvent evaporated to remove the THF and the resulting yellow solid was filtered (washed with water) to afford tert-butyl 4-bromo-2- nitrophenylcarbamate 58 (15.38 g, >100% yield (not dry)). LRMS(ESI): (calc.) 316.1(found) 339.0/341.0 (MNa)+
With potassium carbonate In methanol at 20℃; for 12h;

  • 2
  • [ 55276-43-2 ]
  • [ 1228392-59-3 ]
  • [4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]-carbamic acid di-tert-butyl ester [ No CAS ]
  • [4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 100℃; for 1h; b. [4-(4-Methanesulfonyl^iperazin-l-yl)~2-nitro-phenyl]-carbamic acid di-tert-butyl ester A degassed mixture of di-tert-butyl 4-bromo-2-nitrophenylcarbamate (1 g, 2.4 mmol), 1- methanesulfonyl-piperazine (590 mg, 3.6 mmol), Pd2(dba)3 (220 mg, 0.24 mmol), Xantphos (278 mg, 0.48 mmol) and Cs2C03 (1.56 g, 4.8 mmol) in toluene (30 mL) was heated at 100 C for 1 hour. The reaction was concentrated, and the residue was purified by flash chromatography on silica to obtain a mixture of the title compound and mono-Boc product (755 mg). The mixture was used directly in next step without further purification. MS (ESI): 400 [M-Boc+H]+.
  • 3
  • [ 1228392-59-3 ]
  • [ 1702259-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate; chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II) / toluene / 95 - 105 °C / Inert atmosphere 2.1: hydrogenchloride / toluene; water / 3 h / 20 - 40 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 1 h / 100 °C 4.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 4.2: 2 h / 0 - 20 °C 5.1: hydrogen / tetrahydrofuran; water; methanol / 3 h / 20 °C / 760.05 Torr 6.1: tetrahydrofuran / 1 h / -10 °C
  • 4
  • [ 1228392-59-3 ]
  • [ 335255-43-1 ]
  • 5
  • [ 50606-31-0 ]
  • [ 1228392-59-3 ]
  • C22H32N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.2% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100℃; for 2h;Inert atmosphere; At room temperature and under nitrogen protection,Compound 4A (10.0 g, 24.0 mmol) and <strong>[50606-31-0]methyl piperazine-1-carboxylate</strong> (3.50 g, 24.3 mmol) were dissolved in toluene (50.0 mL).Then anhydrous cesium carbonate (15.7 g, 48.3 mmol), XantPhos (700 mg, 1.21 mmol) and Pd2(dba)3 (1.11 g, 1.21 mmol) were sequentially added to the above reaction solution.The reaction system was heated to 100 degrees Celsius and stirred for 2 hours. After LCMS monitoring showed that the raw materials disappeared, the reaction system was cooled to room temperature.Then water (20 mL) was added to the reaction solution for quenching.The mixture was extracted with ethyl acetate (30 ml×3 times), and the organic phases were combined. The organic phase was washed with saturated brine (20 ml×2 times), then dried over anhydrous sodium sulfate and filtered. Down concentrated.The obtained residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 3/1) to obtain 6.02 g of yellow solid compound 4B (yield: 52.2%).
  • 6
  • [ 1228392-59-3 ]
  • [ 145214-05-7 ]
  • C19H23N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51.4% With tetrakis(triphenylphosphine) palladium(0); In toluene; at 80℃; for 3h;Inert atmosphere; Under the protection of nitrogen at room temperature, compound 4A (1.00 g, 2.40 mmol) was dissolved in toluene (10.0 mL).Subsequently, <strong>[145214-05-7]2-(tributylstannyl)oxazole</strong> (940 mg, 2.61 mmol) and tetrakis(triphenylphosphine)palladium (280 mg, 0.24 mmol) were added to the above solution.The reaction solution was heated to 80 degrees Celsius and stirred for 3 hours.After LCMS monitoring showed that the starting material disappeared, the mixed solution was concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 3/1) to obtain 500 mg of orange solid compound 46A (yield: 51.4%).
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