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Chemical Structure| 885270-30-4 Chemical Structure| 885270-30-4

Structure of 885270-30-4

Chemical Structure| 885270-30-4

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Product Details of [ 885270-30-4 ]

CAS No. :885270-30-4
Formula : C13H16N2O2
M.W : 232.28
SMILES Code : C(=O)(OC(C)(C)C)[N]2C1=CC=CC(=C1C=C2)N
MDL No. :MFCD06656834

Safety of [ 885270-30-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 885270-30-4 ]

* 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 [ 885270-30-4 ]

[ 885270-30-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 913836-24-5 ]
  • [ 885270-30-4 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen;palladium on activated charcoal; In ethanol; at 20℃; under 2585.81 Torr; for 8.0h; To a stirred solution of 1-Boc-4-nitroindole (6.14 g, 23.4 mmol) in EtOH (100 mL) was added 10% Pd/C (614 mg) under N2. The resulting mixture was shaken under hydrogen (H2, 50 psi) at room temperature for 8 h. The mixture was filtered through a pad of Celite, and washed with EtOH. The filtrate was concentrated under reduced pressure to give the product 1-Boc-4-aminoindole as off-white solid (5.23 g, 96% yield). MS (ESI) m/z 233.2
With hydrogen;5% Pd(II)/C(eggshell); In toluene; at 20℃; under 2585.81 Torr; for 7.0h; Step 2: Preparation of 4-amino-indole-1-carboxylic acid tert-butyl ester (3)To a 500 mL Paar shaker hydrogenation flask was charged 118.0 g of toluene solution from Step 1 containing (14.6 g, 0.0555 mol) of <strong>[913836-24-5]4-nitro-indole-1-carboxylic acid tert-butyl ester</strong> (2) and 0.36 g of 5 wt % Pd-C Degussa Type E101 NO/W (50% water wet). The yellow-green mixture was hydrogenated at about 50 psi at room temperature for about 7 hours until no further hydrogen uptake and HPLC analysis showed the reaction to be complete. Note: Batch should be analyzed quickly when hydrogen uptake is complete since indolene by-product forms due to over hydrogenation. (Extended reaction time results in yield loss via over hydrogenation). The mixture was filtered through Celite, washed with toluene, dried by azeotrope distillation, and concentrated to a batch weight of 120 grams of toluene solution of product. This solution was used directly in Step 3.
  • 2
  • [ 885270-30-4 ]
  • [ 16182-04-0 ]
  • [ 1186401-24-0 ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane; at 20℃; To a solution of <strong>[885270-30-4]1-Boc-4-aminoindole</strong> (5.23 g, 22.5 mmol) in CH2Cl2 was added ethyl isothiocyanatoformate (2.95 g, 22.5 mmol), and the resulting mixture was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure and triturated with diethyl ether to give the title compound as off-white solid (8.1 g, 99% yield).
89.4% In toluene; at 20 - 28℃; for 1.0h;Product distribution / selectivity; Step 3: Preparation of tert-butyl 4-(3-ethoxycarbonyl)thioureido)-1H-indole-1-carboxylate (4) To a 3 L four-necked flask equipped with a mechanical stirrer, thermocouple, and N2 inlet tube was added tert-butyl 4-amino-1H-indole-1-carboxylate (121.0 g, 0.521 mole) and toluene (1100 mL). The reaction mixture was stirred at room temperature and a clear solution was formed. To this clear solution, ethyl isothiocyanatoformate (68.3 g, 0.52 mole, 1.0 eq) was added over one hour period keeping internal temperature between 20-28 C. The product precipitated during the addition. HPLC analysis showed the reaction was complete at the end of the addition. The product was filtered off and washed with 1:1 toluene:heptane (800 ml) to give 169.0 g light yellow product in 89.4% yield (100% pure by analytical HPLC)
  • 3
  • [ 913836-24-5 ]
  • [ 885270-30-4 ]
  • [ 885272-42-4 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogen;5% Pd(II)/C(eggshell); In toluene; at 20℃; under 2585.81 Torr; for 3.0h; To a 2.5 liter Paar shaker hydrogenation flask was charged 40.0 g (0.152 mol) of, 500 mL of toluene and 1.0 g of 5 wt % Pd-C Degussa Type E101 NO/W (50% water wet). The yellow-green mixture was hydrogenated at about 50 psi at room temperature for about 3 hours until no further hydrogen uptake and HPLC analysis showed the reaction to be complete. Note: batch should be analyzed quickly when hydrogen uptake is complete since about 5-15% of indolene by-product forms due to over hydrogenation. (Extended reaction time results in yield loss via over hydrogenation). The mixture was filtered through Celite, washed with toluene, and concentrated.Multiple hydrogenation batches were combined and concentrated to 140 gram crude orange oil. The material was purified by chromatography with 25% EtOAc: 75% hexane and eluted to afford 121 gram of pure product as an orange oil in 100 area % by HPLC in an overall yield of 88%. The indolene by-product 12 must be removed in this step otherwise it carries through to later steps.
  • 4
  • [ 5192-23-4 ]
  • [ 49761-82-2 ]
  • [ 885270-30-4 ]
  • 5
  • [ 24424-99-5 ]
  • [ 885270-30-4 ]
  • C18H24N2O4 [ No CAS ]
  • 6
  • [ 885270-30-4 ]
  • tert-butyl 4-((tert-butoxycarbonyl)((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)amino)-6-(2-chloro-pyridin-4-yl)-1H-indole-1-carboxylate [ No CAS ]
  • 7
  • [ 885270-30-4 ]
  • tert-butyl 4-((tert-butoxycarbonyl)((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)amino)-1H-indole-1-carboxylate [ No CAS ]
  • 8
  • [ 885270-30-4 ]
  • tert-butyl 4-((tert-butoxycarbonyl)((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)amino)-6-(2-(methoxycarbonyl)phenyl)-1H-indole-1-carboxylate [ No CAS ]
 

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