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Chemical Structure| 95-20-5
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Product Details of [ 95-20-5 ]

CAS No. :95-20-5 MDL No. :MFCD00005616
Formula : C9H9N Boiling Point : -
Linear Structure Formula :- InChI Key :BHNHHSOHWZKFOX-UHFFFAOYSA-N
M.W : 131.17 Pubchem ID :7224
Synonyms :

Calculated chemistry of [ 95-20-5 ]      Expand+

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) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.18 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.493 mg/ml ; 0.00376 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 [ 95-20-5 ]

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 [ 95-20-5 ]

* 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 [ 95-20-5 ]
  • Downstream synthetic route of [ 95-20-5 ]

[ 95-20-5 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 95-20-5 ]
  • [ 1075-34-9 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: for 0.5 h; Cooling with ice
Stage #2: at 20℃; for 4.5 h;
Step 1. 5-Bromo-2-methyl-7H-indoleTo a solution of 2-methyl-iH-indole (5.0 g, 38.12 mmol) in sulfuric acid (80 mL) was added Ag2S04 (12.5 g, 40.06 mmol) with ice cooling, and the solution was stirred for 30 min. Then Br2 (6.4 g, 40.05 mmol) was added to the solution dropwise over 30 min. After the solution was stirred for 4 h at room temperature, the reaction was then quenched by the addition of water/ice (300 mL). The reaction mixture was extracted with dichloromethane (3 x 200 mL) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-bromo-2-methyl-7H-indole as a light brown solid (6 g, 75percent).LC/MS (ES, m/z): [M+H]+ 211.0'H-NMR (300 MHz, CDC13): δ 11.23 (s, 1Η), 7.56 (s, 1Η), 7.21 (d, / = 8.7 Hz, 1H), 7.07 - 7.09 (m, 1H), 6.11 (s, 1H), 2.38 (s, 3H)
59%
Stage #1: for 0.5 h; Cooling with ice
Stage #2: With bromine In sulfuric acid at 20℃; for 4 h;
Stage #3: With water In sulfuric acid
EXAMPLE 24 2,2,2-Trifluoro-1-(5-(3-(isopropyl(methyl)amino)-6-(1H-tetrazol-5-yl)quinoxalin-2-yl)-2-methyl-1H-indol-3-yl)ethanone Step 1. 5-Bromo-2-methyl-1H-indole To a solution of 2-methyl-1H-indole (5.0 g, 38.12 mmol) in sulfuric acid (80 ml) was added Ag2SO4 (12.5 g, 40.06 mmol) with ice cooling, and the solution was stirred for 30 min. Then Br2 (6.4 g, 40.05 mmol) was added to the solution dropwise over 30 min. After the solution was stirred for 4 h at room temperature, the reaction was quenched by the addition of water/ice (300 ml). The reaction mixture was extracted with dichloromethane (3.x.200 ml) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-bromo-2-methyl-1H-indole as a light brown solid (4.7 g, 59percent).LC/MS (ES, m/z): [M+H]+ 211.01H-NMR (300 MHz, CDCl3): δ 11.23 (s, 1H), 7.56 (s, 1H), 7.21 (d, J=8.7 Hz, 1H), 7.07-7.09 (m, 1H), 6.11 (s, 1H), 2.38 (s, 3H)
Reference: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 161
[2] Patent: US2012/225863, 2012, A1, . Location in patent: Page/Page column 28
  • 2
  • [ 95-20-5 ]
  • [ 68-12-2 ]
  • [ 5416-80-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 1 - 5℃; for 0.333333 h;
Stage #2: at 35℃; for 0.666667 h;
Stage #3: at 95℃; for 0.5 h; Cooling with ice
General procedure: POCl3 (1.73 mL, 18.6 mmol) was slowly added dropwise into stirred and ice-cooled DMF (5.0 mL). The reaction mixture was stirred at 1-5 °C for 20 min, then a solution of corresponding substituted 2-methylindole 6 (15.5 mmol) in DMF (5.0 mL) was slowly added. The resulting reaction mixture was slowly warmed to 35 °C and kept at this temperature for 40 min. It was then allowed to cool down to room temperature. To this mixture, ice (~10 g) was added followed by 5 M NaOH solution (31 mL, 155 mmol). The reaction mixture was heated at 95 °C for 30 min, and then it was allowed to cool down to room temperature. To this mixture, ice (~10 g) was again added, and the resulting reaction mixture was stirred for 30 min. The desired product was collected by filtration and washed several times with water.
90%
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).
87%
Stage #1: at 0℃; for 0.666667 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 1.33333 h;
Stage #3: With water; sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.5 h;
Anhydrous N,N-dimethylformamide (DMF) (12.6 mL, 163.4 mmol) was placed in an N2-purged 250 ml 3-neck round bottom flask and cooled to 0° C. in an ice bath. Phosphorus oxychloride (POCl3, 3.9 mL, 41.84 mmol) was slowly added thereto and stirred at 0° C. for 40 minutes. A solution of 2-methyl-1H-indole (4) (4.8 g, 36.5 mmol) in DMF (7.5 mL) was slowly added thereto while maintaining the temperature at 5° C. or lower. The resulting solution was stirred at 0° C. for 40 minutes, warmed at room temperature, and further stirred for 40 minutes. Then, a few pieces of ice were added to the flask, and a sodium hydroxide (NaOH) solution (16.5 g, 412.5 mmol dissolved in 50 mL of water) was added as droplet form through a dropping funnel while the mixture was vigorously stirred. The resulting solution was heated at 100° C., stirred for 30 minutes, and cooled at room temperature. The resulting pale yellow precipitate was filtered, washed with water, and dried. Then, the product was recrystallized from diethyl ether and hexane to yield a purified product of 2-methyl-1H-indole-3-carbaldehyde (5) as a pale yellow solid (5.0 g, yield 87percent). The 1H NMR spectrum of the resulting 2-methyl-1H-indole-3-carbaldehyde (5) is shown in FIG. 7, and the mass spectrum is shown in FIG. 8. 1H NMR (400 MHz, DMSO-d6) δ ppm: 11.962 (1H, s, —NH), 10.058 (1H, s, —CHO), 8.054-80.33 (1H, dd, J=8.4, 2.0, Ar—H), 7.396-7.373 (1H, dd, J=6.6, 2.4, Ar—H), 7.188-7.130 (2H, m, Ar—H), 2.681 (3H, s, —CH3); ESIMS found: m/z 158.4 [M−H], 160.4 [M+H]+, 182.3 [M+Na]+; Rf=0.29 (hexane:ethyl acetate=1:1).
79%
Stage #1: for 2.5 h; Cooling with ice
Stage #2: at 5℃; for 3 h;
Stage #3: With sodium hydroxide In water; N,N-dimethyl-formamide for 1 h; Cooling with ice; Reflux
Formylation of 2-methy-indole was carried out according to McNab462-Methyl-indole-3-carboxaldchyde. Phosphorus oxychloride (1.44 g. 0.88 ml. 9.4 mmol) was added to ice cooled N, N- dimethyl formamide (2.74 g, 2.88 ml, 37.4 mmol) at 0-5 °C and stirred for 2.5 h. A solution of 2-methylindole (1.12 g. 8.5 mmol) in N,N-dimethylformamide (5 ml) was added drop wise keeping the reaction temperature below 5 °C. Upon completion of the addition, ice (7 g) was added followed by drop wise addition of a solution of sodium hydroxide (3.75 g) in water (10 ml) to give a dull yellow precipitate. The reaction was then heated under reflux for 1 h and refrigerated overnight, during which time precipitation of crude product occurred. The product was filtered, washed with water (450 cm3) and re-filtered to give 2-methyl-N-indole-3- carboxaldehyde.Yield:79percent; 'H NMR (300MHz, DMSO) δ: 12.01 (s, 1H), 10.06 (s, 1H), 8.07 (m, 1H), 7.40 (m, 1H), 7.21-7.13 (m, 2H), 2.69 (s, 3H)
79%
Stage #1: at 0 - 5℃;
Stage #2: With sodium hydroxide In water; N,N-dimethyl-formamide for 1 h; Reflux
Formylation of 2-methy-indole was carried out according to McNab47 . 2-Methyl-indole-3-carboxaldehyde. Phosphorus oxychloride (1.44 g. 0.88 ml. 9.4 mmol) was added to ice cooled N, N- dimethyl formamide (2.74 g, 2.88 ml, 37.4 mmol) at 0-5 °C and stirred for 2.5 h. A solution of 2-methylindole (1.12 g. 8.5 mmol) in N,N-dimethylformamide (5 ml) was added drop wise keeping the reaction temperature below 5 °C. Upon completion of the addition, ice (7 g) was added followed by drop wise addition of a solution of sodium hydroxide (3.75 g) in water (10 ml) to give a dull yellow precipitate. The reaction was then heated under reflux for 1 h and refrigerated overnight, during which timeprecipitation of crude product occurred. The product was filtered, washed withwater (450 cm3) and re-filtered to give 2-methyl-N-indole-3-carboxaldehyde. Yield: 79 percent; 'H NMR (300MHz, DMSO) δ: 12.01 (s, 1H), 10.06 (s,1H), 8.07 (m, 1H), 7.40 (m, 1H), 7.21-7.13 (m, 2H), 2.69 (s, 3H)
63%
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.

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[2] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1014 - 1018
[3] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[4] European Journal of Medicinal Chemistry, 2003, vol. 38, # 1, p. 75 - 87
[5] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1940 - 1956
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  • 3
  • [ 95-20-5 ]
  • [ 110-18-9 ]
  • [ 5416-80-8 ]
YieldReaction ConditionsOperation in experiment
63% With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 41, p. 5618 - 5621
  • 4
  • [ 95-20-5 ]
  • [ 100-61-8 ]
  • [ 5416-80-8 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 42, p. 5187 - 5189
[2] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11924 - 11927
  • 5
  • [ 95-20-5 ]
  • [ 5416-80-8 ]
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[2] Tetrahedron, 1980, vol. 36, p. 2505 - 2512
[3] ChemMedChem, 2012, vol. 7, # 7, p. 1286 - 1294
[4] Tetrahedron, 2013, vol. 69, # 51, p. 10858 - 10868
  • 6
  • [ 95-20-5 ]
  • [ 74-90-8 ]
  • [ 5416-80-8 ]
Reference: [1] Chemische Berichte, 1923, vol. 56, p. 2317
[2] Chemische Berichte, 1923, vol. 56, p. 2060
[3] Biochemical Journal, 1917, vol. 11, p. 60
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 518
  • 7
  • [ 95-20-5 ]
  • [ 67-66-3 ]
  • [ 5416-80-8 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 I, p. 131
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 I, p. 131
[3] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1914, vol. 91, p. 50
[4] Biochemical Journal, 1935, vol. 29, p. 546,549
  • 8
  • [ 95-20-5 ]
  • [ 64-18-6 ]
  • [ 5416-80-8 ]
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  • 9
  • [ 95-20-5 ]
  • [ 110-45-2 ]
  • [ 5416-80-8 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 I, p. 382[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 II, p. 792
  • 10
  • [ 525-58-6 ]
  • [ 7732-18-5 ]
  • [ 95-20-5 ]
  • [ 5416-80-8 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1911, vol. 71, p. 13
  • 11
  • [ 95-20-5 ]
  • [ 7647-01-0 ]
  • [ 60-29-7 ]
  • [ 74-90-8 ]
  • [ 5416-80-8 ]
Reference: [1] Chemische Berichte, 1923, vol. 56, p. 2317
[2] Chemische Berichte, 1923, vol. 56, p. 2060
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 518
  • 12
  • [ 95-20-5 ]
  • [ 7647-01-0 ]
  • [ 74-90-8 ]
  • [ 67-66-3 ]
  • [ 5416-80-8 ]
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[2] Chemische Berichte, 1923, vol. 56, p. 2060
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 518
  • 13
  • [ 95-20-5 ]
  • [ 67-66-3 ]
  • [ 141-52-6 ]
  • [ 5416-80-8 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 I, p. 131
  • 14
  • [ 95-20-5 ]
  • [ 60-29-7 ]
  • [ 638-49-3 ]
  • [ 141-52-6 ]
  • [ 5416-80-8 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 I, p. 382[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1907, vol. <5> 16 II, p. 792
  • 15
  • [ 95-20-5 ]
  • [ 75-03-6 ]
  • [ 40876-94-6 ]
YieldReaction ConditionsOperation in experiment
83% With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12 h; Example 1Synthesis of JWH4511 -Ethyl-2-methylindole[0150] To a mixture of 0.20 g (1.52 mmol) of 2-methylindole, 0.38 g (6.89 mmol) of KOH in DMSO (6 mL) was added 0.24 mL (3.04 mmol) of iodoethane. The mixture was stirred at room temperature for 12 hours, quenched by the addition of 15 mL of H20, and extracted with ethyl acetate (2 X 15 mL). The combined organic extracts were washed with water (10 mL), brine (20 mL), dried (MgS04), filtered and concentrated in vacuo. The crude product was purified by column chromatography (ether/ petroleum ether 0.5:9.5) to give 0.20g (83 percent) of the desired product as a red oil.
Reference: [1] Patent: WO2012/24670, 2012, A2, . Location in patent: Page/Page column 43
[2] Synthesis, 1981, # 5, p. 389 - 390
[3] Organic Letters, 2017, vol. 19, # 17, p. 4680 - 4683
  • 16
  • [ 95-20-5 ]
  • [ 74-96-4 ]
  • [ 40876-94-6 ]
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[2] Chemical Communications, 2012, vol. 48, # 47, p. 5928 - 5930
  • 17
  • [ 95-20-5 ]
  • [ 64-67-5 ]
  • [ 40876-94-6 ]
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  • 18
  • [ 95-20-5 ]
  • [ 2731-06-8 ]
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[5] Journal of the American Chemical Society, 1959, vol. 81, p. 1203,1206
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[9] Patent: CN106674079, 2017, A,
  • 19
  • [ 95-20-5 ]
  • [ 32588-36-6 ]
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  • 20
  • [ 95-20-5 ]
  • [ 1912-43-2 ]
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[2] Justus Liebigs Annalen der Chemie, 1933, vol. 500, p. 42,45
  • 21
  • [ 95-20-5 ]
  • [ 50-00-0 ]
  • [ 1912-43-2 ]
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[2] DRP/DRBP Org.Chem.,
[3] DRP/DRBP Org.Chem.,
  • 22
  • [ 623-73-4 ]
  • [ 95-20-5 ]
  • [ 1912-43-2 ]
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  • 23
  • [ 95-20-5 ]
  • [ 73430-27-0 ]
  • [ 2826-91-7 ]
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[2] European Journal of Organic Chemistry, 2012, # 6, p. 1230 - 1236
  • 24
  • [ 95-20-5 ]
  • [ 82781-92-8 ]
  • [ 2826-91-7 ]
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  • 25
  • [ 95-20-5 ]
  • [ 2826-91-7 ]
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  • 26
  • [ 95-20-5 ]
  • [ 4498-74-2 ]
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  • 27
  • [ 95-20-5 ]
  • [ 603-81-6 ]
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  • 28
  • [ 95-20-5 ]
  • [ 92623-83-1 ]
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[2] Patent: CN108752257, 2018, A,
  • 29
  • [ 95-20-5 ]
  • [ 100-07-2 ]
  • [ 92623-83-1 ]
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  • 30
  • [ 95-20-5 ]
  • [ 215734-58-0 ]
  • [ 602-04-0 ]
  • [ 78581-99-4 ]
YieldReaction ConditionsOperation in experiment
9% at 110℃; for 35 h; The reaction mixturewas evaporated in vacuo. The solid was worked up with EtOH (3–4 mL). The precipitate of tris(2-methylindol-3-yl)methane(4b) was filtered off and rinsed with EtOH. Yield 9percent, mp > 300 (lit. [7] mp > 300). 1 NMR spectrum (400 MHz,DMSO-d6, , ppm, J/Hz): 1.92 (9, s, CH3), 6.09 (1, s, CH), 6.60 (3, ddd, J = 7.9, 7.2, 1.0, H-5), 6.84–6.90 (6, m,H-6, 7), 7.16 (3, dd, J = 7.9, 1.2, H-4), 10.37 (3, s, NH). Mass spectrum (EI, 70 eV), m/z (Irel, percent): 404 (33), 403 (M+, 89),402 (22), 272 (75), 271 (15), 257 (86), 256 (32).
Reference: [1] Chemistry of Natural Compounds, 2017, vol. 53, # 3, p. 519 - 522[2] Khim. Prir. Soedin., 2017, # 3, p. 441 - 443,3
  • 31
  • [ 95-20-5 ]
  • [ 86704-55-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2167 - 2171
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