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Chemical Structure| 17826-04-9
Chemical Structure| 17826-04-9
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Product Details of [ 17826-04-9 ]

CAS No. :17826-04-9 MDL No. :MFCD00792689
Formula : C9H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :WCCLQCBKBPTODV-UHFFFAOYSA-N
M.W : 224.05 Pubchem ID :2794830
Synonyms :
6-Bromoindole-3-carboxaldehyde

Calculated chemistry of [ 17826-04-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.39
TPSA : 32.86 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.74
Log Po/w (MLOGP) : 1.6
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.176 mg/ml ; 0.000787 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.67 mg/ml ; 0.00299 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.0182 mg/ml ; 0.0000811 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 17826-04-9 ]

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 [ 17826-04-9 ]

* 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.

  • Upstream synthesis route of [ 17826-04-9 ]
  • Downstream synthetic route of [ 17826-04-9 ]

[ 17826-04-9 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 17826-04-9 ]
  • [ 101774-27-0 ]
Reference: [1] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497
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  • [ 52415-29-9 ]
  • [ 68-12-2 ]
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: for 0.333333 h; Cooling with ice
Stage #2: at 20℃; for 1.5 h;
General procedure: To a dried two-neck round-bottom flask containing DMF (0.7mL for 1.10mmol of starting material) chilled in an ice bath, POCl3 (1.95 equiv) was added slowly. After stirring for 20min, a solution of an indole derivative (1.0 equiv) in DMF (3mL for 1.10mmol of starting material) was added dropwise. The reaction was allowed to warm to room temperature and allowed to stir for 1.5h. The reaction was quenched by adding ice followed by 1N NaOH (40mL) dropwise in an ice bath. The crude mixture was allowed to stand at room temperature and the precipitate formed was filtered to afford the 3-formyl-indole derivative product.
47% at 0 - 20℃; for 2.5 h; At 0 , the POCl3(2.0mL) was added dropwise to DMF (8.0mL) and stirred for 30 minutes after the dropping Compound 1 (3.0g, 15.3mmol), DMF (2.0ml) mixed solution, the end of the dropwise addition, naturally warmed to room temperature and stirred for 2 hours .After completion of the reaction, the reaction solution was poured into ice water, saturated sodium bicarbonate solution was adjusted to about pH 8.By filtration, the filtrate was collected, concentrated under reduced pressure to give a pale yellow solid compound B(1.60g, 47percent).
25%
Stage #1: at 0 - 8℃; for 0.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 2 h;
13a) 6-Bromo-lH-indole-3-carbaldehydeThis compound was prepared according to the general procedure described by M. A. Wuonola et. al. (J. Org. Chem., (1994), 59_, 6823-6827). To ice-water cooled N,N-dimethylformamide (10 mL) was slowly added phosphorus oxychloride (3.2 mL, 34.6 mmol) with stirring under a nitrogen atmosphere while maintaining the temperature between 0 0C and 8 0C. The reaction mixture was stirred at 0 0C for 30 min. To the cold reaction mixture was slowly added a solution of 6-bromoindole (5.5 g, 28.1 mmol) in N,N-dimethylformamide (28 mL) while maintaining the temperature of the reaction mixture between 0 0C and 10 0C. The ice-water bath was removed and the reaction mixture was allowed to stir at room temperature for 2 hours. The viscous mixture was poured into ice-water (250 g) and the pη of the cold aqueous mixture was adjusted to ~7 (litmus paper) with 1 N sodium hydroxide. The mixture was allowed to stand at room temperature overnight. The mixture was filtered to give a pink solid which was washed with water and recrystallized from ethyl alcohol to give 1.6 g (25percent) of 6-bromo-l/f-indole-3-carbaldehyde as a pale tan solid. 1H NMR (dβ- DMSO, 400 MHz): δ 12.20 (br s, IH), 9.91 (s, IH), 8.31 (d, J = 3 Hz, IH), 8.00 (d, J = 9 Hz, IH), 7.69 (d, J = 2 Hz, IH), 7.34 (dd, J = 8, 2 Hz, IH).
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4621 - 4628
[2] Chinese Chemical Letters, 2010, vol. 21, # 8, p. 889 - 891
[3] Marine Drugs, 2013, vol. 11, # 5, p. 1427 - 1439
[4] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 344 - 367
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 22, p. 5600 - 5603[6] Angew. Chem., 2014, vol. 126, # 22, p. 5706 - 5709,4
[7] Journal of Chemical Crystallography, 2009, vol. 39, # 5, p. 329 - 336
[8] Patent: CN105440016, 2016, A, . Location in patent: Paragraph 0040; 0041
[9] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 102
[10] Liebigs Annalen der Chemie, 1985, # 9, p. 1882 - 1894
[11] Journal of Organic Chemistry, 1994, vol. 59, # 22, p. 6823 - 6827
[12] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 4, p. 569 - 572
[13] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 2, p. 363 - 371
[14] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1301 - 1305
[15] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 13, p. 4783 - 4792
[16] Chemical Biology and Drug Design, 2011, vol. 77, # 3, p. 182 - 188
[17] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2362 - 2372
[18] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497
[19] Organic Letters, 2013, vol. 15, # 24, p. 6262 - 6265
[20] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00390
[21] Synthesis (Germany), 2017, vol. 49, # 11, p. 2562 - 2562
[22] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 184 - 194
[23] Organic Letters, 2017, vol. 19, # 10, p. 2502 - 2505
[24] Green Chemistry, 2017, vol. 19, # 13, p. 2952 - 2956
[25] Patent: WO2009/140769, 2009, A1, . Location in patent: Page/Page column 60
[26] Patent: WO2009/135299, 2009, A1, . Location in patent: Page/Page column 80-81
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YieldReaction ConditionsOperation in experiment
73% With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 5 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
  • 4
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  • [ 100-97-0 ]
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YieldReaction ConditionsOperation in experiment
73% With aluminum (III) chloride In N,N-dimethyl-formamide at 120℃; for 5 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; 0116-0119
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Reference: [1] Patent: WO2010/151737, 2010, A2, . Location in patent: Page/Page column 142
  • 6
  • [ 52415-29-9 ]
  • [ 100-61-8 ]
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Reference: [1] Chemical Communications, 2012, vol. 48, # 42, p. 5187 - 5189
  • 7
  • [ 487-89-8 ]
  • [ 877-03-2 ]
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  • [ 17900-95-7 ]
Reference: [1] Environmental Toxicology and Chemistry, 2001, vol. 20, # 3, p. 589 - 596
  • 8
  • [ 60956-26-5 ]
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Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 8, p. 889 - 891
  • 9
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 10, p. 1831 - 1839
  • 10
  • [ 184637-11-4 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 10, p. 1831 - 1839
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 10, p. 1831 - 1839
  • 12
  • [ 78508-22-2 ]
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Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 8, p. 889 - 891
  • 13
  • [ 487-89-8 ]
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Reference: [1] Journal of Chemical Ecology, 1997, vol. 23, # 11, p. 2507 - 2521
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  • [ 99910-50-6 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 11, p. 2817 - 2822
  • 15
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  • [ 224434-83-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 4, p. 569 - 572
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 2, p. 363 - 371
[3] Patent: WO2010/151737, 2010, A2, . Location in patent: Page/Page column 142
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5897 - 5900
[5] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497
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YieldReaction ConditionsOperation in experiment
51%
Stage #1: at 20℃; for 0.0833333 h;
Stage #2: at 20℃; Inert atmosphere
13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite.(R). and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51percent based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. 1H NMR (J6-DMSO, 400 MHz): δ 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)".
Reference: [1] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 102-103
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