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[ CAS No. 6960-42-5 ] {[proInfo.proName]}

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Chemical Structure| 6960-42-5
Chemical Structure| 6960-42-5
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Product Details of [ 6960-42-5 ]

CAS No. :6960-42-5 MDL No. :MFCD00005683
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LZJGQIVWUKFTRD-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :23396
Synonyms :

Calculated chemistry of [ 6960-42-5 ]

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) : 1.45
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 : 1.22

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 : 1.78

Safety of [ 6960-42-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6960-42-5 ]

* 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 [ 6960-42-5 ]
  • Downstream synthetic route of [ 6960-42-5 ]

[ 6960-42-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 6960-45-8 ]
  • [ 6960-42-5 ]
YieldReaction ConditionsOperation in experiment
69% at 194℃; for 2 h; Example 4: Preparation of Compound 4 (7-Nitro-1H indole); The compound 3 (1.63 g, 7.91 mmol) was dissolved in quinoline (13 mL), and then CuO (0.19 g) was added therein. The mixture was stirred and heated to 194 °C. During the heating process, gas was generated. After 2 hr, there was no gas generated, the reaction was completed, and the TLC test was used to confirm the completion of the reaction. Then, the solution was poured into an HCl solution formulated by HCl (21.3 mL) and cold water (42.6 mL), and black precipitates were formed after stirring. The resulting solution was filtered, and the black precipitates and the filtrate were extracted by ether. Both phases of the extraction was collected, and respectively washed with saturated NaHCO3 solution and water. After dehydration by Na2SO4, the organic layer was filtered and concentrated to obtain a yellow solid. Then, the yellow solid was re-crystallized in EtOH to obtain a needle-shaped light-yellow solid, compound 4 (0.87 g, 69percent). mp 96-97 °C(lit. 95-96 °C); 1H NMR (200 MHz, CDCl3) δ6.63 (dd, J= 2.2, 1.0 Hz, 1H, ArH), 7.08-7.18 (m, 1H, ArH), 7.32 (t, J = 3.0 Hz, 1H, ArH), 7.90 (d, J = 7.8 Hz, 1H, ArH), 8.08 (d, J = 8.1 Hz, 1H, ArH), 9.88 (s, 1H, NH); 13C NMR (50 MHz, acetone-d6) δ103.7, 118.9, 119.2, 128.4, 129.1, 129.3, 132.9, 133.5; MS (EI) m/z 162 (M+, 100percent), 116 (M-46, 87percent), 104 (M-58, 41percent), 89 (M-73, 53percent).
Reference: [1] Patent: EP2366687, 2011, A2, . Location in patent: Page/Page column 8; 10-11
[2] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[3] Journal of Organic Chemistry, 1957, vol. 22, p. 84
[4] Journal and Proceedings of the Royal Society of New South Wales, 1938, vol. 72, p. 209,216
[5] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[6] Journal of Organic Chemistry, 1957, vol. 22, p. 84
[7] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837
  • 2
  • [ 53924-05-3 ]
  • [ 6960-42-5 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 36, p. 12898 - 12899
  • 3
  • [ 1826-67-1 ]
  • [ 528-29-0 ]
  • [ 6960-42-5 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 3, p. 568 - 574
[2] Organic Letters, 2013, vol. 15, # 18, p. 4730 - 4733
  • 4
  • [ 6960-46-9 ]
  • [ 6960-42-5 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[2] Journal of Organic Chemistry, 1957, vol. 22, p. 84
[3] Patent: EP2366687, 2011, A2,
[4] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837
  • 5
  • [ 292853-66-8 ]
  • [ 6960-42-5 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[2] Journal of Organic Chemistry, 1957, vol. 22, p. 84
[3] Patent: EP2366687, 2011, A2,
  • 6
  • [ 127-17-3 ]
  • [ 3034-19-3 ]
  • [ 6960-42-5 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 6, p. 984 - 986
  • 7
  • [ 6293-87-4 ]
  • [ 6960-42-5 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837
  • 8
  • [ 6960-42-5 ]
  • [ 5192-04-1 ]
YieldReaction ConditionsOperation in experiment
99% With ammonium formate In ethanol for 1 h; Heating / reflux By following the procedures as described in Preparation 7 (Scheme VII, Step A) 7-nitro indole is dissolved in ethanol and. to this mixture added ammonium formate (lOeq) and a catalytic amount of 10percent palladium on carbon. This mixture is then heated to reflux for 1 hr before it is cooled, filtered through celite and evaporated to provide the product as a purple solid (99percent).
99% With ammonium formate In ethanol for 1 h; Heating / reflux lH-Indol-7-ylamine Dissolve 7-nitroindole in ethanol and add ammonium formate (10 equivalents) and a catalytic amount of 10percent palladium on carbon. Heat the mixture to reflux for 1 hr before cooling, filter through celite, and evaporate to provide the product as a purple solid (99percent).
99% With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 20℃; for 12 h; Schlenk technique General procedure: Procedure B: A mixture of nitro compounds 1 (0.50 mmol) and Pd/C (10 wtpercent palladium on activated carbon paste and 50 percent moisture, 5 wtpercent wet Pd/C based on starting material 1) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature. Followed by addition of H2NNH2·H2O (50 mg, 1.0 mmol, 2.0 equiv) and the mixture was stirred at room temperature until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.
96.7% With hydrogen In ethanol at 27℃; 1H-Indol-7-ylamine Charge a 3-gal autoclave with 7-nitroindole (250 g, 1.542 moles), 2B-3 ethyl alcohol (5.0 L), and 10 percent Pd/C (50.0 g). Stir at 50 psi H2 for 2 h at <27 °C. When the reaction is deemed complete, filter the reactor contents through Celite followed by concentration of the filtrate to dryness to yield 197.0 g (96.7 percent) of the title compound as purple solid. IH- NMR (CD30D, 300MHz) 8 7.16 (d, 1H), 7.00 (dd, 1H), 6.81 (t, 1H), 6.50 (dd, 1H), 6.37 (d, 1H).

Reference: [1] Patent: WO2004/67529, 2004, A1, . Location in patent: Page 75 - 76
[2] Patent: WO2005/92854, 2005, A1, . Location in patent: Page/Page column 53
[3] Green Chemistry, 2017, vol. 19, # 3, p. 809 - 815
[4] Synthetic Communications, 2018, vol. 48, # 19, p. 2475 - 2484
[5] Patent: WO2005/92854, 2005, A1, . Location in patent: Page/Page column 56-57
[6] Tetrahedron Letters, 1995, vol. 36, # 14, p. 2411 - 2414
[7] European Journal of Organic Chemistry, 2009, # 28, p. 4854 - 4866
[8] Tetrahedron, 2008, vol. 64, # 3, p. 568 - 574
[9] Organic and Biomolecular Chemistry, 2014, vol. 13, # 3, p. 925 - 937
[10] Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1942 - 1954
[11] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3789 - 3799
[12] Journal of Medicinal Chemistry, 2002, vol. 45, # 22, p. 4913 - 4922
[13] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6443 - 6445
[14] Patent: US2004/63733, 2004, A1,
[15] Chemical Communications, 2009, # 41, p. 6279 - 6281
[16] Patent: EP2366687, 2011, A2, . Location in patent: Page/Page column 24-25
[17] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5909 - 5915
[18] Patent: WO2012/115479, 2012, A2, . Location in patent: Page/Page column 19-20
[19] Organic Letters, 2013, vol. 15, # 18, p. 4730 - 4733
[20] Synthesis (Germany), 2015, vol. 47, # 6, p. 861 - 870
[21] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837
[22] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
[23] RSC Advances, 2018, vol. 8, # 16, p. 8898 - 8909
[24] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137
  • 9
  • [ 6960-42-5 ]
  • [ 68-12-2 ]
  • [ 10553-14-7 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 0℃; for 0.0833333 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 3 h; Inert atmosphere
Stage #3: With potassium hydroxide In water; N,N-dimethyl-formamide for 15 h;
POCl3 (0.418 mL, 3.13 mmol) was added dropwise to N,N-dimethylformamide (DMF) (2.08 mL) at 0°C under an argon atmosphere. The mixture was stirred for 5 min, and then 7-nitroindole (200 mg, 1.25 mmol) was added as a DMF solution (10 mL per 1 g indole). The mixture was then allowed to warm to room temperature and stirred for 3 h. Then, 3.8 M aq. KOH (3.29 mL, 12.5 mmol) was added, and the mixture was stirred for 15 h. Saturated aq. NaHCO3 and EtOAc were then added to the mixture until the mixture became clear and the organic layer separated. The mixture was extracted with EtOAc, and the organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/EtOAc=1/5) to afford 9l (228 mg, 1.20 mmol, 96percent) as a yellow amorphous solid.
80%
Stage #1: at 0℃; for 1 h;
Stage #2: at 20℃; for 5 h;
Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667 h;
General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k).
Reference: [1] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 8, p. 810 - 817
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[3] Tetrahedron Letters, 2009, vol. 50, # 1, p. 75 - 76
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 23, p. 7541 - 7551
[5] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2362 - 2372
  • 10
  • [ 50-00-0 ]
  • [ 6960-42-5 ]
  • [ 10553-14-7 ]
YieldReaction ConditionsOperation in experiment
70% With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 20 h; General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37percent aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25percent aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 molpercent), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane–EtOAc).
Reference: [1] Synlett, 2017, vol. 28, # 19, p. 2670 - 2674
  • 11
  • [ 6960-42-5 ]
  • [ 100-97-0 ]
  • [ 10553-14-7 ]
YieldReaction ConditionsOperation in experiment
70% With aluminum (III) chloride In N,N-dimethyl-formamide at 120℃; for 20 h; General procedure: A method for synthesizing compound III-1 wherein R1, R2 and R3 are simultaneously hydrogen in the formula III, the method comprising the steps of:(1) Add to a 50 mL round bottom flask1.0mmol indole(In the formula I, R1, R2, and R3 are both hydrogen) and1.0 mmol (0.140 g) of hexamethylenetetramine, then 2 mL of N,N-dimethylformamide (DMF), stirred in a magnetic stirrer to dissolve the solid, followed by the addition of 0.05 mmol (0.012 g) of crystalline trichloride Aluminum, connected to a reflux condenser, heated at 120 ° C, the reaction progress was monitored by TLC, and the reaction was cooled to room temperature after 1 h to prepare a suspension;(2) The suspension prepared in the step (1) is suction filtered with a funnel padded with diatomaceous earth.The filter cake was washed well with ethyl acetate, suction filtered, and the above operation was repeated until the filtrate had no product, and all the filtrates were combined.Dilute with 15 mL of saturated saline solution, disperse and separate the layers, and the aqueous layer was further extracted with ethyl acetate three times.Each time 10 mL, the ethyl acetate layer was combined and washed with 10 mL of 2 mol/L diluted hydrochloric acid.Wash with 10 mL of saturated sodium bicarbonate solution, and finally wash with 10 mL of saturated brine.The washed ethyl acetate layer was dried over anhydrous sodium sulfate, and after drying, the desiccant was filtered off.Then use a rotary evaporator to recover the solvent to concentrate the product, and finally,The residue is subjected to silica gel column chromatography using a mixture of n-hexane-ethyl acetate (V/V = 2:1) as an eluent to obtain a purified product.The mass of the compound III-indole-3-carbaldehyde is 0.137g,The product yield was 94percent.
Reference: [1] Patent: CN108329249, 2018, A, . Location in patent: Paragraph 0041-0044; 0136-0139
  • 12
  • [ 6960-42-5 ]
  • [ 10553-14-7 ]
Reference: [1] Patent: US2002/25957, 2002, A1,
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