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[ CAS No. 4769-97-5 ] {[proInfo.proName]}

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Chemical Structure| 4769-97-5
Chemical Structure| 4769-97-5
Structure of 4769-97-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4769-97-5 ]

CAS No. :4769-97-5 MDL No. :MFCD00010056
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LAVZKLJDKGRZJG-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :145766
Synonyms :

Calculated chemistry of [ 4769-97-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.12
TPSA : 61.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 0.38
Log Po/w (SILICOS-IT) : 0.32
Consensus Log Po/w : 1.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.491 mg/ml ; 0.00303 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.259 mg/ml ; 0.0016 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.65
Solubility : 0.36 mg/ml ; 0.00222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 4769-97-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4769-97-5 ]

* 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.

  • Upstream synthesis route of [ 4769-97-5 ]
  • Downstream synthetic route of [ 4769-97-5 ]

[ 4769-97-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 4769-97-5 ]
  • [ 5192-23-4 ]
YieldReaction ConditionsOperation in experiment
89% With iron; ammonium chloride In water; isopropyl alcohol for 2 h; Reflux; Inert atmosphere General procedure: Method A. Nitrocompound (1 mmol) was dissolve in a 0.1 M mixture of IPA: H2O(4:1) and iron powder (Fe, 3 mmol), ammonium chloride (NH4Cl,2 mmol) were added and refluxed for two hours. After cooling down to room temperature reaction mixture was filtered through celite, extracted with EtOAc (25 mL x 3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure and purified by column chromatography.
Reference: [1] Patent: US6255306, 2001, B1,
[2] Chemistry - A European Journal, 2014, vol. 20, # 11, p. 3050 - 3060
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2280 - 2287
[4] RSC Advances, 2014, vol. 4, # 43, p. 22567 - 22574
[5] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738
[6] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 13 - 23
[7] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4128 - 4139
[8] Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 7004 - 7011
[9] Patent: WO2009/34581, 2009, A1, . Location in patent: Page/Page column 24
[10] Patent: WO2011/23081, 2011, A1, . Location in patent: Page/Page column 55-56
[11] Patent: WO2012/28106, 2012, A1, . Location in patent: Page/Page column 50
[12] ACS Catalysis, 2014, vol. 4, # 5, p. 1441 - 1450
[13] RSC Advances, 2016, vol. 6, # 63, p. 58805 - 58812
[14] Catalysis Science and Technology, 2018, vol. 8, # 5, p. 1454 - 1467
  • 2
  • [ 4769-97-5 ]
  • [ 7439-89-6 ]
  • [ 5192-23-4 ]
YieldReaction ConditionsOperation in experiment
82% With acetic acid In methanol; ethanol A.
4-Aminoindole.
Iron powder (1.20 g, 21.58 mmol) and acetic acid (2.47 mL, 43.19 mmol) are added to a solution of 4-nitroindole (1.0 g, 6.17 mmol) in ethanol (20 mL).
The resulting suspension is heated to reflux for 14 hours.
The ethanol is removed by rotary evaporation and the residue is partitioned between water and ethyl acetate.
The ethyl acetate layer is dried over magnesium sulfate, filtered, and the solvents removed by rotary evaporation.
The crude residue is purified via silica gel column chromatography using 1percent methanol/methylene chloride as the eluent.
The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.815 g of 4-aminoindole as an orange solid (82percent yield).
Reference: [1] Patent: US6162818, 2000, A,
  • 3
  • [ 78283-21-3 ]
  • [ 5192-23-4 ]
  • [ 4769-97-5 ]
  • [ 78283-23-5 ]
  • [ 78283-24-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738
[2] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738
[3] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738
  • 4
  • [ 23622-32-4 ]
  • [ 4769-96-4 ]
  • [ 4769-97-5 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 2117 - 2120[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 11, p. 2420 - 2423
[3] Journal of Organic Chemistry USSR (English Translation), 1983, p. 2117 - 2120[4] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 11, p. 2420 - 2423
  • 5
  • [ 4769-97-5 ]
  • [ 84807-26-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
  • 6
  • [ 4769-97-5 ]
  • [ 89245-41-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3696 - 3708
  • 7
  • [ 4769-97-5 ]
  • [ 85696-95-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3417 - 3427
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[4] Tetrahedron Letters, 2017, vol. 58, # 13, p. 1324 - 1325
  • 8
  • [ 4769-97-5 ]
  • [ 24424-99-5 ]
  • [ 913836-24-5 ]
YieldReaction ConditionsOperation in experiment
95% at 0 - 20℃; To a stirred solution of 4-nitroindole (4.0 g, 24.6 mmol) in CH2Cl2 (50 mL) were added catalytic amount of DMAP (Catalyst) and Boc2O (5.9 g, 27.1 mmol) at 0° C., and the resulting reaction mixture was stirred at room temperature for additional 3 h. The mixture was diluted with CH2Cl2, and washed with water. The organic phase was dried over MgSO4. The solvent was removed under reduced pressure to give 1-Boc-4-nitroindole as white solid (6.14 g, 95percent yield). MS (ESI) m/z 262.1
95.8% at 20℃; for 1.75 h; Step 1:
Preparation of 4-Nitro-indole-1-carboxylic acid tert-butyl ester (2)
To a 5 L four-necked round bottom flask equipped with mechanical stirrer, nitrogen inlet, thermocouple, and condenser was charged 182.3 g (1.124 mol) of 4-nitroindole, 1400 mL toluene, and 2.7 g of DMAP. At room temperature, solid BOC2O (270.0 g 1.237 mol, 1.10 eq) was added in portions over about 45 minutes to the stirring mixture while maintaining moderate gas evolution.
After stirring the resulting solution for 1 hour, HPLC analysis showed the reaction to be complete with no starting material.
The batch was quenched with 500 mL water, transferred to a separatory funnel and the phases were split.
The organic layer was washed with 500 mL brine, concentrated to a slurry, diluted with 1000 ml heptane, filtered, and washed with fresh heptane.
The filter cake was dried under vacuum at RT to constant weight to afford 206.0 gram of pale yellow solid.
A second crop of 20.0 gram of product was isolated as post-precipitate from the mother liquors.
The overall yield was 226.0 gram, 95.8percent yield of pale yellow solid (100 area percent HPLC).
Reference: [1] Patent: US2009/227575, 2009, A1, . Location in patent: Page/Page column 20
[2] Patent: US2010/36123, 2010, A1, . Location in patent: Page/Page column 4; 5; 7; 8
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