Structure of 4771-49-7
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CAS No. : | 4771-49-7 |
Formula : | C10H9NO |
M.W : | 159.18 |
SMILES Code : | O=CC1=CNC2=C1C=CC(C)=C2 |
MDL No. : | MFCD00049347 |
InChI Key : | LZERQSJGPXFAKB-UHFFFAOYSA-N |
Pubchem ID : | 4777902 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
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 ? Topological Polar Surface Area: Calculated from | 32.86 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 3.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.99 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.5 |
Solubility | 0.503 mg/ml ; 0.00316 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.19 |
Solubility | 1.02 mg/ml ; 0.00642 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.61 |
Solubility | 0.0393 mg/ml ; 0.000247 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -5.94 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.18 |
* 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.
Yield | Reaction Conditions | Operation 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]+). |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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+) |
Yield | Reaction Conditions | Operation 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) |
Yield | Reaction Conditions | Operation 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+) |
Yield | Reaction Conditions | Operation 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) |
Yield | Reaction Conditions | Operation 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) |
Yield | Reaction Conditions | Operation 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) |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 1 Preparation of (3E)-5-(6-Methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone A mixture of 4.77 g. of <strong>[4771-49-7]6-methylindole-3-carboxaldehyde</strong>, 4.24 g. of dimethylcreatinine, and 50 ml. of piperidine was heated at reflux for 24 hours. The cooled suspension was poured into 250 ml. of water, and the yellow precipitate was collected by filtration, washed with water and dried in vacuo and afforded 7.0 g. of crude 5-(6-methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone. Recrystallization from acetonitrile gave 4.50 g. of (3E)-5-(6-methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone, melting point 227°-228°. Calcd. for C16 H18 N4 O: C, 68.07; H, 6.43; N, 19.84. Found: C, 67.86; H, 6.38; N, 19.68. Mass spectrum, m/e 282; UV (95percent ethanol): 233 nm.(epsilon23,600); 275 nm (8300), 392 nm (23,400); NMR (100 mHz, DMSO-d6): delta 8.61 (s, 1H, H-2), 6.36 (broad, 1H, --CH=C--CO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
159.5 g (89%) | With pyridine; acetic anhydride; | EXAMPLE 31 Alpha-acetamido-6-methylindole-3-acrylic acid ethylester A 3-l. three-necked flask, equipped with a mechanical stirrer, a thermometer and a dropping funnel with pressure-equalizing arm was charged with 100 g (0.63 mol) of <strong>[4771-49-7]6-methylindole-3-carboxaldehyde</strong>, 119 g (0.63 mol) of acetamidomalonic acid monoethylester and 500 ml of pyridine. The mixture was stirred and kept at 15° with a cold water bath while 175 ml of acetic anhydride was added over 15 minutes. The yellow solution was stirred at room temperature for 3 hours. Then an additional portion of 36 g (0.19 mol) of acetamidomalonic acid monoethyl ester was added and stirring at room temperature was continued for 22 hours before 1 kg of ice was added. The temperature fell to -10° and the product began to precipitate. The suspension was stirred at room temperature for 5 hours and poured into 2 1 of water. After 20 minutes, the precipitate was collected by suction filtration, washed with water and dried at 50° in an air oven overnight to afford 159.5 g (89percent) of crude product as yellow crystals, m.p. 159°-162° (sinters at 75°). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 22℃; for 3h; | 63.1. 6-Methyl-1H-indole-3-carbaldehyde oxime To a solution of <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> (0.96 g, Lit. 20) 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 the title compound (0.96 g) as a pink solid. MS: 175.3 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With formic acid; hydroxylamine hydrochloride; sodium formate; for 1h;Heating / reflux; | Example 4; 1. Synthesis of indole derivatives; 1) Synthesis of 3-cyanoindole derivatives; [Show Image] Nine objective compounds were prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-6-ether in dimethyl sulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order (the following Table 2). In addition, XO-CH172 and XO-CH183 (R is a 2-methyl group or a 5-methoxy group, respectively) were prepared from the step (2) using the corresponding aldehydes purchased.; XO-CH186; XO-CH180 (1.14g, 7.16 mmol) was dissolved in formic acid (11 mL), to the solution were added hydroxylamine hydrochloride (0.63 g, 9.1 mmol) and sodium formate (0.90 g, 13 mmol). The mixture was heated for reflux for an hour. To the reaction mixture was added water under ice-cooling, and the mixture was stirred for a while. The solid was collected by filtration and dried 60°C under reduced pressure to give XO-CH186 as a red-black solid (0.85 g, 76percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: NaH (60percent dispersion in mineral oil, 20.00 mmol, 0.48 g) wasa dded portionwise to a stirred solution of the aldehyde 4 (10.00 mmol) in anhydrous THF (25 mL) cooled in an ice bath. The resulting mixture was then slowly allowed to warm to r.t. After stirring for 30 min, PhSO2Cl (12.00 mmol) (CH3COCl 12.00 mmol for5f) in anhydrous THF (5 mL) was added dropwise. When TLC monitoring showed that the starting material 4 had disappeared, the reaction mixture was evaporated under reduced pressure to remove the solvent and was then diluted with ice water (50 mL). Solid products were filtered off and recrystallized from acetone/petroleum ether (60-90 °C) to give the desired intermediate 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.82% | With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h; | Add III-3 (1.00g, 6.29mmol), DMAP (154mg, 1.26mmol), DIEA (3.16mL, 18.87mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C A solution of p-toluenesulfonyl chloride (IV-3, 1.44 g, 7.56 mmol) in 10 mL of acetonitrile was added, and stirring was continued for 2 h under low temperature conditions.TLC monitoring of raw material reactionsCompletely, concentrate the reaction solution, dissolve it with 30 mL of ethyl acetate, wash with 40 mL of water, and extract twice with ethyl acetate (20 mL×2)The organic phase is washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate; filtered, filtered, and then filtered and evaporated.After drying, 1.57gBeige solid V-7,The yield was 79.82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.3% | With lithium aluminium tetrahydride; In tetrahydrofuran; for 8.5h;Reflux; | A solution of <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> (4.00 g, 25.1 mmol) in THF (50 mL) was added to a refluxing mixture of LiA1H4 (2.098 g, 55.3 mmol) in THF (50 mL) (reflux condenser fitted to a two neck flask) over 30 mm. The reaction mixture was refluxed for 8 hours, cooled to room temperature and treated with ether (50 mL). Thereaction mixture was acidified to pH 3 with iN HC1 while cooling in an ice bath. The reaction mixture was diluted with EtOAc (125 mL), poured into a separatory funnel and washed with water (2X 50 mL) and saturated aqueous NaC1 solution (50 mL), dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to give crude product. The crude product was dissolved in a small amount of DCM and charged to an ISCO silica gel 80G column which was eluted over a 25 mm gradient with 0percent-50percent ethyl acetate/heptane to give 3,6-dimethyl-1H-indole (2.6 g, 71.3 percent yield). LC retention time 0.96 mm [1A]. MS (E) m/z: 146 (M-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.93% | With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h; | Add III-3 (1.00g, 6.29mmol), DMAP (154mg, 1.26mmol), DIEA (3.12mL, 18.87mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C 4-chlorophenylsulfonyl chloride (IV-5, 1.60g, 7.55mmol) in 10mL acetonitrile solution, after the addition was completed, stirring was continued for 2 hours under low temperature conditions.TLC monitoring of raw material reactionsCompletely, concentrate the reaction solution, dissolve with 30 mL of ethyl acetate, wash with 40 mL of water, and then extract twice with ethyl acetate (20 mL×2). The organic phase is combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate The filtrate is spin-dried and subjected to column chromatography (petroleum ether:Ethyl acetate = 10:1 rinse),After drying, 1.71 g of a brownish yellow solid V-11 was obtained.The yield was 91.93%. |
Tags: 4771-49-7 synthesis path| 4771-49-7 SDS| 4771-49-7 COA| 4771-49-7 purity| 4771-49-7 application| 4771-49-7 NMR| 4771-49-7 COA| 4771-49-7 structure
A140574 [52562-50-2]
5-Methyl-1H-indole-3-carbaldehyde
Similarity: 1.00
A185448 [141835-34-9]
5-Phenyl-1H-indole-3-carbaldehyde
Similarity: 1.00
A654623 [4771-48-6]
4-Methyl-1H-indole-3-carbaldehyde
Similarity: 0.98
A248249 [5416-80-8]
2-Methyl-1H-indole-3-carbaldehyde
Similarity: 0.96
A140574 [52562-50-2]
5-Methyl-1H-indole-3-carbaldehyde
Similarity: 1.00
A185448 [141835-34-9]
5-Phenyl-1H-indole-3-carbaldehyde
Similarity: 1.00
A654623 [4771-48-6]
4-Methyl-1H-indole-3-carbaldehyde
Similarity: 0.98
A248249 [5416-80-8]
2-Methyl-1H-indole-3-carbaldehyde
Similarity: 0.96
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