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[ CAS No. 4771-49-7 ] {[proInfo.proName]}

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Chemical Structure| 4771-49-7
Chemical Structure| 4771-49-7
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Product Details of [ 4771-49-7 ]

CAS No. :4771-49-7 MDL No. :MFCD00049347
Formula : C10H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :LZERQSJGPXFAKB-UHFFFAOYSA-N
M.W : 159.18 Pubchem ID :4777902
Synonyms :

Calculated chemistry of [ 4771-49-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.65
TPSA : 32.86 ?2

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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 1.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.503 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.02 mg/ml ; 0.00642 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0393 mg/ml ; 0.000247 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 4771-49-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4771-49-7 ]

* 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.

  • Downstream synthetic route of [ 4771-49-7 ]

[ 4771-49-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 123-75-1 ]
  • [ 4771-49-7 ]
  • [ 75629-47-9 ]
  • 2
  • [ 79-24-3 ]
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  • [ 566200-36-0 ]
  • 3
  • [ 4771-49-7 ]
  • [ 940304-80-3 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 22℃; for 3h; 10.1. To a solution of <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> (0.96 g, Lit. 5) in ethanol (30 ml) was added at 22° C. hydroxylamine hydrochloride (0.46 g) and sodium acetate (0.54 g) and the mixture was stirred for 3 h. The mixture was evaporated and the residue triturated with water and dichloromethane/n-heptane (1:1) and dried to give <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> oxime (0.96 g) as a pink solid. MS: 175.3 ([M+H]+).
  • 4
  • [ 4771-49-7 ]
  • 2,4,6-trimethyl-N-[1-methyl-2-(6-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide [ No CAS ]
  • 6
  • [ 4771-49-7 ]
  • 1-(3-chloro-phenyl)-2-[1-methyl-2-(6-methyl-1<i>H</i>-indol-3-yl)-ethylamino]-ethanol [ No CAS ]
  • 7
  • sodium metabisulfite [ No CAS ]
  • [ 4771-49-7 ]
  • thallium(III) trifluoroacetate [ No CAS ]
  • [ 338760-54-6 ]
YieldReaction ConditionsOperation in experiment
283 mg (79%) With potassium iodide; In diethyl ether; water; trifluoroacetic acid; (a) Preparation of 6-methyl-4-iodo-indole-3-carboxaldehyde A solution of thallium (III) trifluoroacetate (1 g 1.84 mmol) in trifluoroacetic acid (15 mL) was added to 6-methyl-indole-3-carboxaldehyde (200 mg, 1.25 mmol) and the resulting mixture was stirred at 30° C. for 2 h. The solvent was removed under vacuum (rotary evaporator). To the residue was added an aqueous solution of potassium iodide (2 g, 12 mmol, in 20 mL of water) and the mixture was stirred at room temperature overnight. Solid sodium meta-bisulfite was added to the reaction mixture until it turned yellow. The mixture was basified with aqueous NaOH solution and was extracted repeatedly from diethyl ether. The combined organic was washed with brine and was dried over magnesium sulfate. Evaporation of solvent gave the crude product, which was purified by flash chromatography by using EtOAc as eluent. The product, 6-methyl-4-iodo-indole-3-carboxaldehyde was isolated as solid to yield 283 mg (79percent) of the desired product. MS: 286.
YieldReaction ConditionsOperation in experiment
EXAMPLE 32 (E)-3-(6-Methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 32) Process 1 Substantially the same procedure as in Process 1 of Example 15 was repeated using 6-methylindole (1.15 g) to give 6-methylindole-3-carboxaldehyde (1.34 g). 1H-NMR (270 MHz, CDCl3) delta2.47 (s, 3H), 7.10 (d, J=8.0 Hz, 1H), 7.24 (brs, 1H), 7.75 (d, J=2.6 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 9.99 (s, 1H), 10.55 (brs, 1H) EI-MS m/z=159 (M+)
  • 9
  • [ 110-89-4 ]
  • [ 191671-30-4 ]
  • [ 108-20-3 ]
  • [ 4771-49-7 ]
  • [ 191670-92-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol; EXAMPLE 106 (Z)-2-(beta-D-Glucosylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 106) 2-(beta-D-Glucosylthio)-3',4',5'-trimethoxy-acetophenone (1.01 g) obtained in Reference Example 17 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.40 g) were dissolved in ethanol (10 ml), and piperidine (0.21 g) was added thereto, followed by heating under reflux for 24 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethanol and purified by preparative HPLC (YMC pack ODS, SH-343-5, S-5, 120A, 250*20 mm, acetonitrile:water=40:60). The elude was concentrated under reduced pressure and the residue was recrystallized from a mixed solvent of ethanol and isopropyl ether (1:1) to give Compound 106 (322.2 mg). 1 H-NMR (270 MHz, DMSO-d6) delta2.40 (s, 3H), 2.78 (m, 1H), 3.16-3.32 (m, 5H), 3.79 (s, 3H), 3.80 (s, 3H), 3.81 (s, 3H), 4.24 (t, J=5.6 Hz, 1H), 4.76 (d, J=8.6 Hz, 1H), 4.82 (d, J=4.6 Hz, 1H), 5.09 (d, J=2.9 Hz, 1H), 5.46 (d, J=5.0 Hz, 1H), 6.94 (d, J=8.3 Hz, 1H), 7.09 (s, 2H), 7.26 (s, 1H), 7.33 (d, J=8.3 Hz, 1H), 7.52 (s, 1H), 8.12 (d, J=2.5 Hz, 1H), 11.73 (s, 1H) FAB-MS m/z=545 (M+ +1) Elemental Analysis: C27 H31 NO9 S.0.8H2 O Calcd.(percent): C, 57.91; H, 5.87; N, 2.50 Found (percent): C, 57.88; H, 5.77; N, 2.40
In ethanol; Example 14 (Z)-2-(beta-D-Glucosylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 14) 2-(beta-D-Glucosylthio)-3',4',5'-trimethoxyacetophenone (1.01 g) obtained in Reference Example 17 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.40 g) were dissolved in ethanol (10 ml), and piperidine (0.21 g) was added thereto, followed by heating under reflux for 24 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethanol and purified by preparative HPLC (YMC pack ODS, SH-343-5, S-5, 120A, 250 x 20 mm, acetonitrile:water = 40:60). The elude was concentrated under reduced pressure and the residue was recrystallized from a mixed solvent of ethanol and isopropyl ether (1:1) to give Compound 14 (322.2 mg). 1H-NMR (270 MHz, DMSO-d6) delta 2.40 (s, 3H), 2.78 (m, 1H), 3.16-3.32 (m, 5H), 3.79 (s, 3H), 3.80 (s, 3H), 3.81 (s, 3H), 4.24 (t, J = 5.6 Hz, 1H), 4.76 (d, J = 8.6 Hz, 1H), 4.82 (d, J = 4.6 Hz, 1H), 5.09 (d, J = 2.9 Hz, 1H), 5.46 (d, J = 5.0 Hz, 1H), 6.94 (d, J = 8.3 Hz, 1H), 7.09 (s, 2H), 7.26 (s, 1H), 7.33 (d, J = 8.3 Hz, 1H), 7.52 (s, 1H), 8.12 (d, J = 2.5 Hz, 1H), 11.73 (s, 1H) FAB-MS m/z = 545 (M++1)
  • 10
  • [ 110-89-4 ]
  • [ 191671-29-1 ]
  • [ 4771-49-7 ]
  • (Z)-2-(2,3-dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; hexane; ethyl acetate; EXAMPLE 120 (Z)-2-(2,3-Dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 120) 2-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxy-acetophenone (1.58 g) obtained in Reference Example 16 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (975.0 mg) were dissolved in ethanol (10 ml), and piperidine (494.5 mg) was added thereto, followed by heating under reflux for 36 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) to give Compound 120 (1.23 g). 1 H-NMR (270 MHz, CDCl3) delta2.36 (s, 1H), 2.46 (s, 3H), 2.82 (dd, J=13.9, 8.9 Hz, 1H), 3.08 (dd, J=13.9, 4.0 Hz, 1H), 3.55 (m, 1H), 3.68 (m, 1H), 3.77 (m, 1H), 3.87 (s, 6H), 3.97 (s, 3H), 4.16 (s, 1H), 7.04 (d, J=7.7 Hz, 1H), 7.10 (s, 2H), 7.24 (s, 1H), 7.41 (d, J=7.7 Hz, 1H), 7.96 (s, 1H), 8.54 (d, J=3.0 Hz, 1H), 8.96 (s, 1H) EI-MS m/z=457 (M+) Elemental Analysis: C24 H27 NO6 S.0.2H2 O Calcd.(percent): C, 62.51; H, 5.99; N, 3.04 Found (percent): C, 62.46; H, 6.11; N, 2.95
In ethanol; hexane; ethyl acetate; Example 28 (Z)-2-(2,3-Dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 28) 2-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxyacetophenone (1.58 g) obtained in Reference Example 16 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (975.0 mg) were dissolved in ethanol (10 ml), and piperidine (494.5 mg) was added thereto, followed by heating under reflux for 36 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) to give Compound 28 (1.23 g). 1H-NMR (270 MHz, CDCl3) delta 2.36 (s, 1H), 2.46 (s, 3H), 2.82 (dd, J = 13.9, 8.9 Hz, 1H), 3.08 (dd, J = 13.9, 4.0 Hz, 1H), 3.55 (m, 1H), 3.68 (m, 1H), 3.77 (m, 1H), 3.87 (s, 6H), 3.97 (s, 3H), 4.16 (s, 1H), 7.04 (d, J = 7.7 Hz, 1H), 7.10 (s, 2H), 7.24 (s, 1H), 7.41 (d, J = 7.7 Hz, 1H), 7.96 (s, 1H), 8.54 (d, J = 3.0 Hz, 1H), 8.96 (s, 1H) EI-MS m/z = 457 (M+)
  • 11
  • [ 110-89-4 ]
  • [ 191671-34-8 ]
  • [ 4771-49-7 ]
  • [ 191670-98-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol; hexane; water; ethyl acetate; EXAMPLE 112 (E)-2-(3,4-Dihydroxybutyl)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 112) 5,6-Dihydroxy-1-(3,4,5-trimethoxyphenyl)hexan-1-one (870.0 mg) obtained in Reference Example 21 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (465.0 mg) were dissolved in ethanol (8 ml), and piperidine (288.8 mg) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) and then from a mixed solvent of ethanol and water (1:1) to give Compound 112 (142.7 mg). 1 H-NMR (270 MHz, CDCl3) delta1.70-1.95 (m, 2H), 2.36 (brs, 1H), 2.47 (s, 3H), 2.87 (m, 1H), 3.03 (m, 1H), 3.54 (m, 1H), 3.65 (m, 1H), 3.77 (m, 1H), 3.88 (s, 6H), 3.96 (s, 3H), 4.04 (brs, 1H), 7.00 (s, 2H), 7.02 (d, J=8.8 Hz, 1H), 7.22 (s, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.75 (s, 1H), 7.79 (d, J=2.3 Hz, 1H), 8.79 (s, 1H) FAB-MS m/z=440 (M+ +1) Elemental Analysis: C25 H29 NO6.0.3H2 O Calcd.(percent): C, 67.49; H, 6.71; N, 3.15 Found (percent): C, 67.55; H, 6.93; N, 3.15
In ethanol; hexane; water; ethyl acetate; Example 20 (E)-2-(3,4-Dihydroxybutyl)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 20) 5,6-Dihydroxy-1-(3,4,5-trimethoxyphenyl)hexan-1-one (870.0 mg) obtained in Reference Example 21 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (465.0 mg) were dissolved in ethanol (8 ml), and piperidine (288.8 mg) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) and then from a mixed solvent of ethanol and water (1:1) to give Compound 20 (142.7 mg). 1H-NMR (270 MHz, CDCl3) delta 1.70-1.95 (m, 2H), 2.36 (brs, 1H), 2.47 (s, 3H), 2.87 (m, 1H), 3.03 (m, 1H), 3.54 (m, 1H), 3.65 (m, 1H), 3.77 (m, 1H), 3.88 (s, 6H), 3.96 (s, 3H), 4.04 (brs, 1H), 7.00 (s, 2H), 7.02 (d, J = 8.8 Hz, 1H), 7.22 (s, 1H), 7.41 (d, J = 8.8 Hz, 1H), 7.75 (s, 1H), 7.79 (d, J = 2.3 Hz, 1H), 8.79 (s, 1H) FAB-MS m/z = 440 (M++1)
  • 12
  • [ 110-89-4 ]
  • [ 191671-38-2 ]
  • [ 4771-49-7 ]
  • [ 243636-31-9 ]
YieldReaction ConditionsOperation in experiment
In ethanol; EXAMPLE 128 3-(6-Methylindol-3-yl)-2-[(2S),(3R)-2,3,4-trihydroxy-butylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 128) 3',4',5'-Trimethoxy-2-[(2S),(3R)-2,3,4-trihydroxy-butylthio]acetophenone (1.73 g) obtained in Reference Example 22 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 26 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 128 (1.22 g). 1 H-NMR (270 MHz, CDCl3) delta2.43 (s, 3H), 2.96 (dd, J=13.6, 8.7 Hz, 1H), 3.10 (dd, J=13.6, 4.0 Hz, 1H), 3.23 (brs, 1H), 3.53-3.82 (m, 5H), 3.84 (s, 6H), 3.96 (s, 3H), 4.84 (brs, 1H), 7.00 (d, J=8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J=2.6 Hz, 1H), 9.39 (brs, 1H) FAB-MS m/z=488 (M+ +1) Elemental Analysis: C25 H29 NO7 S Calcd.(percent): C, 61.59; H, 6.00; N, 2.87 Found (percent): C, 61.26; H, 6.12; N, 2.82
In ethanol; Example 36 3-(6-Methylindol-3-yl)-2-[(2S),(3R)-2,3,4-trihydroxybutylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 36) 3',4',5'-Trimethoxy-2-[(2S),(3R)-2,3,4-trihydroxybutylthio]acetophenone (1.73 g) obtained in Reference Example 22 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 26 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 36 (1.22 g). 1H-NMR (270 MHz, CDCl3) delta 2.43 (s, 3H), 2.96 (dd, J = 13.6, 8.7 Hz, 1H), 3.10 (dd, J = 13.6, 4.0 Hz, 1H), 3.23 (brs, 1H), 3.53-3.82 (m, 5H), 3.84 (s, 6H), 3.96 (s, 3H), 4.84 (brs, 1H), 7.00 (d, J = 8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.36 (d, J = 8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J = 2.6 Hz, 1H), 9.39 (brs, 1H) FAB-MS m/z = 488 (M++1)
  • 13
  • [ 110-89-4 ]
  • [ 191671-42-8 ]
  • [ 4771-49-7 ]
  • [ 243636-32-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; EXAMPLE 129 3-(6-Methylindol-3-yl)-2-[(2R),(3S)-2,3,4-trihydroxy-butylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 129) 3',4',5'-Trimethoxy-2-[(2R),(3S)-2,3,4-trihydroxy-butylthio]acetophenone (1.73 g) obtained in Reference Example 23 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 129 (1.12 g). 1 H-NMR (270 MHz, CDCl3) delta2.43 (s, 3H), 2.95 (dd, J=13.6, 8.7 Hz, 1H), 3.10 (dd, J=13.6, 4.0 Hz, 1H), 3.17 (brs, 1H), 3.53 (d, J=6.3 Hz, 1H), 3.64-3.82 (m, 4H), 3.84 (s, 6H), 3.96 (s, 3H), 4.83 (d, J=4.0 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J 2.6 Hz, 1H), 9.36 (brs, 1H) FAB-MS m/z=488 (M+ +1) Elemental Analysis: C25 H29 NO7 S Calcd.(percent): C, 61.59; H, 6.00; N, 2.87 Found (percent): C, 61.56; H, 6.14; N, 2.82
In ethanol; Example 37 3-(6-Methylindol-3-yl)-2-[(2R),(3S)-2,3,4-trihydroxybutylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 37) 3',4',5'-Trimethoxy-2-[(2R),(3S)-2,3,4-trihydroxybutylthio]acetophenone (1.73 g) obtained in Reference Example 23 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 37 (1.12 g). 1H-NMR (270 MHz, CDCl3) delta 2.43 (s, 3H), 2.95 (dd, J = 13.6, 8.7 Hz, 1H), 3.10 (dd, J = 13.6, 4.0 Hz, 1H), 3.17 (brs, 1H), 3.53 (d, J = 6.3 Hz, 1H), 3.64-3.82 (m, 4H), 3.84 (s, 6H), 3.96 (s, 3H), 4.83 (d, J = 4.0 Hz, 1H), 7.01 (d, J = 8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.37 (d, J = 8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J = 2.6 Hz, 1H), 9.36 (brs, 1H) FAB-MS m/z = 488 (M++1)
  • 14
  • CH3 I [ No CAS ]
  • [ 4771-49-7 ]
  • 1,6-dimethyl-1H-indole-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With NaH; In N,N-dimethyl-formamide; EXAMPLE 1 3-(1,6-dimethyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3yl)-pyrrole-2,5-dione A solution of the known <strong>[4771-49-7]6-methyl-1H-indole-3-carboxaldehyde</strong> (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3 I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2 O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL*3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97percent).
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Chemical Structure| 5416-80-8

[ 5416-80-8 ]

2-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.96

; ;