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[ CAS No. 933-67-5 ] {[proInfo.proName]}

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Chemical Structure| 933-67-5
Chemical Structure| 933-67-5
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Product Details of [ 933-67-5 ]

CAS No. :933-67-5 MDL No. :MFCD00005684
Formula : C9H9N Boiling Point : -
Linear Structure Formula :- InChI Key :KGWPHCDTOLQQEP-UHFFFAOYSA-N
M.W : 131.17 Pubchem ID :70275
Synonyms :
7-Methyl-1H-indole
Chemical Name :7-Methyl-1H-indole

Calculated chemistry of [ 933-67-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.26
TPSA : 15.79 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) : -5.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.84
Solubility : 0.191 mg/ml ; 0.00145 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.542 mg/ml ; 0.00413 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0305 mg/ml ; 0.000232 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 933-67-5 ]

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 [ 933-67-5 ]

* 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 [ 933-67-5 ]
  • Downstream synthetic route of [ 933-67-5 ]

[ 933-67-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 933-67-5 ]
  • [ 65673-86-1 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide
General procedure: 5.1.24. 7-Fluoro-2,3-dihydro-1H-indole (15f) 7-Fluoro-1H-indole (20.0 g, 148 mmol) was dissolved in acetic acid (60 mL) and sodium cyanoborohydride (18.7 g, 296 mmol) was added in portions. The mixture was stirred for 2 h and then poured into 1500 mL of 2 M aqueous NaOH solution. The mixture was extracted with CH2Cl2. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure to give the title compound (20.0 g, 98percent). 1H NMR (400 MHz, CDCl3) δ 3.08 (2H, t, J = 8.4 Hz), 3.62 (2H, t, J = 8.4 Hz), 6.62-6.66 (1H, m), 6.78-6.83 (1H, m), 6.90 (1H, dd, J = 7.6, 0.4 Hz).
94% With sodium cyanoborohydride In acetic acid; ethyl acetate A.
2,3-Dihydro-7-methylindole.
To a stirred solution of 7-methylindole (10.27 g, 78.3 mmol) in glacial acetic acid (50 mL) is added sodium cyanoborohydride (6.33 g, 100.7 mmol) portionwise over a 5 minute period.
The reaction solution is allowed to stir for 1 hour.
The solution is diluted with water (500 mL) and basified with 50percent sodium hydroxide solution.
The basic solution is extracted with three 250 mL portions of diethyl ether.
The organic fractions are combined, dried over anhydrous potassium carbonate, filtered and evaporated to give a pink oil.
The oil is purified by silica gel column chromatography using 20percent ethyl acetate/hexanes as eluent to give 11.63 g of 2,3-dihydro-7-methylindole as a colorless oil (94percent yield).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1649 - 1666
[2] Patent: US6162818, 2000, A,
[3] Journal of Chemical Research, Miniprint, 1996, # 12, p. 2936 - 2945
[4] Chemical Communications, 2017, vol. 53, # 66, p. 9262 - 9264
[5] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724
[6] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[7] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[8] Patent: WO2011/51398, 2011, A1, . Location in patent: Page/Page column 10-11
[9] Organic and Biomolecular Chemistry, 2013, vol. 11, # 7, p. 1209 - 1215
[10] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437
  • 2
  • [ 84312-25-4 ]
  • [ 933-67-5 ]
  • [ 13708-12-8 ]
  • [ 62-53-3 ]
  • [ 100-61-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 377 - 380
  • 3
  • [ 933-67-5 ]
  • [ 100-97-0 ]
  • [ 4771-50-0 ]
YieldReaction ConditionsOperation in experiment
89% With iodine; oxygen; pyrographite In N,N-dimethyl-formamide at 120℃; for 1.5 h; General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 molpercent) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product.
88% With aluminum (III) chloride In N,N-dimethyl-formamide at 120℃; for 1.5 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] Tetrahedron Letters, 2017, vol. 58, # 30, p. 2877 - 2880
[2] Patent: CN108329249, 2018, A, . Location in patent: Paragraph 0041-0044; 0066-0069
  • 4
  • [ 933-67-5 ]
  • [ 50-00-0 ]
  • [ 4771-50-0 ]
YieldReaction ConditionsOperation in experiment
93% With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 1.5 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
  • 5
  • [ 933-67-5 ]
  • [ 68-12-2 ]
  • [ 4771-50-0 ]
Reference: [1] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[2] Chemical Communications, 2012, vol. 48, # 51, p. 6351 - 6353
[3] Journal of the Chemical Society, 1965, p. 7165,7174
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1301 - 1305
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3780 - 3790
[6] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
[7] Green Chemistry, 2017, vol. 19, # 13, p. 2952 - 2956
[8] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 666 - 680
[9] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6647 - 6651
  • 6
  • [ 933-67-5 ]
  • [ 100-61-8 ]
  • [ 4771-50-0 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11924 - 11927
[2] Chemical Communications, 2012, vol. 48, # 42, p. 5187 - 5189
  • 7
  • [ 933-67-5 ]
  • [ 67-68-5 ]
  • [ 4771-50-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 41, p. 7092 - 7095
  • 8
  • [ 933-67-5 ]
  • [ 67-66-3 ]
  • [ 4771-50-0 ]
Reference: [1] Biochemical Journal, 1935, vol. 29, p. 546,549
  • 9
  • [ 933-67-5 ]
  • [ 4771-50-0 ]
Reference: [1] Biochemical Journal, 1935, vol. 29, p. 546,549
  • 10
  • [ 933-67-5 ]
  • [ 30448-16-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2734 - 2737
[2] Journal of the Chemical Society, 1954, p. 1651
[3] Journal of the Chemical Society, 1954, p. 1651
[4] Patent: WO2009/125923, 2009, A2,
  • 11
  • [ 933-67-5 ]
  • [ 407-25-0 ]
  • [ 30448-16-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7067 - 7083
  • 12
  • [ 933-67-5 ]
  • [ 68-12-2 ]
  • [ 30448-16-9 ]
Reference: [1] Journal of medicinal chemistry, 1991, vol. 34, # 1, p. 140 - 151
  • 13
  • [ 933-67-5 ]
  • [ 15719-64-9 ]
  • [ 30448-16-9 ]
Reference: [1] Chemische Berichte, 1926, vol. 59, p. 2755
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