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5-Methoxyindole

5-Methoxyindole

5-Methoxyindole

CAS No.: 1006-94-6

Category Products

Cat.NO.:A105085 Purity:99%

Product Details of 5-Methoxyindole

CAS No. :	1006-94-6
Formula :	C₉H₉NO
M.W :	147.17
SMILES Code :	COC1=CC2=C(NC=C2)C=C1
MDL No. :	MFCD00005674
InChI Key :	DWAQDRSOVMLGRQ-UHFFFAOYSA-N
Pubchem ID :	13872

Safety of 5-Methoxyindole

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 5-Methoxyindole

* 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 [ 1006-94-6 ]

[ 1006-94-6 ] Synthesis Path-Downstream 1~14

1
[ 1006-94-6 ]
[ 15441-06-2 ]
methyl 3-(5-methoxy-1H-indol-1-yl)propanoate [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 3123 – 3125.

2
[ 1006-94-6 ]
[ 30982-08-2 ]
3-(2′-methoxycarbonyl-2′-propenyl)-5-methoxylindole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 – 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 – 8422.

3
[ 1006-94-6 ]
[ 3471-31-6 ]

References: [1]Phytochemistry,2007,vol. 68,p. 1651 – 1663.
[2]Journal of the American Chemical Society,2012,vol. 134,p. 10815 – 10818.
[3]Patent: CN103664974,2016,B .
[4]Patent: CN104311469,2016,B .

4
[ 1006-94-6 ]
[ 39974-94-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1793 – 1798.
[2]Organic Letters,2013,vol. 15,p. 2636 – 2639.
[3]Angewandte Chemie – International Edition,2014,vol. 53,p. 11051 – 11055.

Angew. Chem.,2014,vol. 126,p. 11231 – 11235,5.
[4]European Journal of Medicinal Chemistry,2015,vol. 99,p. 125 – 137.
[5]RSC Advances,2015,vol. 5,p. 68128 – 68135.
[6]Chemical Biology and Drug Design,2015,vol. 86,p. 731 – 745.
[7]Journal of Medicinal Chemistry,2016,vol. 59,p. 5264 – 5283.
[8]ChemMedChem,2016,vol. 11,p. 1446 – 1458.
[9]European Journal of Medicinal Chemistry,2017,vol. 132,p. 310 – 321.
[10]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7404 – 7410.
[11]RSC Advances,2016,vol. 6,p. 30412 – 30424.
[12]European Journal of Medicinal Chemistry,2018,vol. 156,p. 722 – 737.
[13]Organic Letters,2019,vol. 21,p. 2602 – 2605.
[14]Organic Letters,2019,vol. 21,p. 5862 – 5866.
[15]Organic Letters,2019,vol. 21,p. 7702 – 7707.

5
[ 1006-94-6 ]
[ 941-91-3 ]
[ 1335032-97-7 ]

References: [1]European Journal of Organic Chemistry,2011,p. 5077 – 5088.

6
[ 1006-94-6 ]
[ 54439-75-7 ]
[ 1428330-29-3 ]

Yield	Reaction Conditions	Operation in experiment
10%		General procedure: (a) A solution of 3 (16.1 mmol) in 40 ml of glacial acetic acid was refluxed during 20 h. The reaction mixture was cooled down, a yellowish mixture of 2 and 5 was filtered off and washed thoroughly with hot ethanol. The yields of 2a, b, e, and f containing 15e20percent of the respective 5 (evidenced by the presence of the 1H NMR signal about 5.7 ppm) varied between 5percent (2e/5e), 40percent (2a/5a), 74percent (2f/5f), and 80percent (2b/5b). (b) A solution of 5-methoxyindole (3 mmol), 2-chloro-4(5)-methoxybenzaldehyde (3 mmol) and hydroiodic acid (1.4 mmol)(57percentwater solution) in 20 ml of acetonitrilewas refluxed under Ar for 15 h. After evaporation of the solvent, the residue was washed by methanol, filtered and washed with acetonitrile. The resulting mixtures of 2c/5c (10percent yield) and 2d/5d (4percent yield) were used in the next step without further purification. Derivative 5e was isolated by crystallization of the mixture of 2e and 5e from DMSO as colorless crystals involving one molecule of DMSO. C32H26Cl2N2O5S1. Unit cell parameters: a¼13.4133(4), b¼8.6773(2), c¼15.3735(4), b¼101.709(1), space group P 21/c. Deposition number CCDC 905653. The mixtures were used in the next step without further purification.The mixture of 2 and 5 (2.3 mmol), CuI (2.3 mmol), and tetrabutylammonium hydroxide (5.13 mmol) (40percent methanol solution) were suspended in 30 ml of freshly distilled DMF under Ar and heated at 120 C during 24 h. The mixturewas cooled down to room temperature, and the yellow precipitatewas filtered off andwashed with MeCN. Pure products can be obtained by crystallization from benzonitrile.4.2.3.3 2,7,11,16-Tetramethoxydibenzo[2,3; 5,6]pyrrolizino[1,7-bc]indolo[1,2,3-lm]carbazole (1c) Yellow microcrystals from benzonitrile, 10percent yield, sublime above 300 °C. Calcd C34H24N2O4: C (77.85percent), H (4.61percent), N (5.34percent). Found: C (77.89percent), H (4.50percent), N (5.37percent).

References: [1]Tetrahedron,2013,vol. 69,p. 3302 – 3307.

7
[ 1006-94-6 ]
[ 54439-75-7 ]
[ 1433946-20-3 ]
[ 1433946-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen iodide; In water; acetonitrile; for 15h;Reflux; Inert atmosphere;	(a) A solution of 3 (16.1 mmol) in 40 ml of glacial acetic acid was refluxed during 20 h. The reaction mixture was cooled down, a yellowish mixture of 2 and 5 was filtered off and washed thoroughly with hot ethanol. The yields of 2a, b, e, and f containing 15e20percent of the respective 5 (evidenced by the presence of the 1H NMR signal about 5.7 ppm) varied between 5percent (2e/5e), 40percent (2a/5a), 74percent (2f/5f), and 80percent (2b/5b). The mixtures were used in the next step without further purification. (b) A solution of 5-methoxyindole (3 mmol), 2-chloro-4(5)-methoxybenzaldehyde (3 mmol) and hydroiodic acid (1.4 mmol)(57percentwater solution) in 20 ml of acetonitrilewas refluxed under Ar for 15 h. After evaporation of the solvent, the residue was washed by methanol, filtered and washed with acetonitrile. The resulting mixtures of 2c/5c (10percent yield) and 2d/5d (4percent yield) were used in the next step without further purification. Derivative 5e was isolated by crystallization of the mixture of 2e and 5e from DMSO as colorless crystals involving one molecule of DMSO. C32H26Cl2N2O5S1. Unit cell parameters: a¼13.4133(4), b¼8.6773(2), c¼15.3735(4), b¼101.709(1), space group P 21/c. Deposition number CCDC 905653.

References: [1]Tetrahedron,2013,vol. 69,p. 3302 – 3307.

8
[ 1006-94-6 ]
[ 521-73-3 ]
4-hydroxy-4-(5-methoxy-1H-indol-3-yl)isoquinoline-1,3(2H,4H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: A heterogeneous mixture of <strong>[521-73-3]isoquinoline-1,3,4-trione</strong>(17.5 mg, 0.1 mmol), indole (14.0 mg, 0.12 mmol) and alginic acid (1.76 mg,0.01 mmol, purchased from Sigma Aldrich) in H2O (0.2 mL) was stirred for 24 h(monitored by TLC). Afterwards, the reaction mixture was concentrated under reduced pressure to leave the crude residue which was purified by column chromatography over silica-gel using ethyl acetate/hexane as a mixture of solvent to give the pure compound 3aa in75% yield (21.9 mg) as a white solid.4-Hydroxy-4-(1H-indol-3-yl)isoquinoline-1,3(2H,4H)-dione (3aa): yield 75%; mp:188-190 C; Rf = 0.25 (EtOAc/hexane = 1:3); 1H NMR (400 MHz, acetone-d6) d10.24 (br s, 1H, NH), 10.10 (br s, 1H, NH), 8.14 (d, J = 7.8 Hz, 1H), 7.89 (d,J = 7.8 Hz, 1H), 7.76-7.79 (m, 2H), 7.59-7.63 (m, 1H), 7.36 (d, J = 8.2 Hz, 1H),7.06-7.10 (m, 1H), 6.96-7.00 (m, 1H), 6.65-6.66 (m, 1H), 5.66 (br s, 1H, OH); 13CNMR (100 MHz, acetone-d6) d 175.0 (CO), 164.7 (CO), 144.3, 138.0, 134.7,129.2, 128.2, 127.9, 125.8, 125.8, 124.8, 122.6, 122.4, 121.7, 120.1, 112.4, 74.7(C-4, quaternary); HRMS (ESI) m/z calcd For C17H12N2O3 [M+Na]+: 315.0897.Found 315.0953.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 6003 – 6007.

9
[ 1006-94-6 ]
[ 110677-45-7 ]
9-{4-[bis(5-methoxy-1H-indol-3-yl)methyl]phenyl}-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride; In tetrahydrofuran; methanol; at 20℃; for 2h;	5-Methoxyindole (I) (1.42 g, 9.6 mmol) and concentrated hydrochloricacid (2 ml) were slowly added to tetrahydrofuran(1.1 ml) and methanol (11 ml) solution of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1) (0.99 g, 3.6 mmol), and the mixture was stirredfor 2 h at room temperature. The resulting solutionwas poured intowater and filtered. The precipitate was dissolved in ethylacetateand washed with 10% NaOH solution. The separated organic layerwas dried over anhydrous Na2SO4. The crude product was purifiedby crystallization from diethyl ether to afford the product as brightyellow crystals. Yield 1.52 g, 76%. 1H NMR spectrum (300 MHz,DMSO, δ, ppm): 10.76 (s, 2H, NH), 8.23 (d, J 7.7 Hz, 2H, Ar), 7.67 (d,J 8.3 Hz, 4H), 7.53 (d, J 8.3 Hz, 2H, Ar) 7.44-7.22 (m, 8H, Ar), 6.99(d, J 2.3 Hz, 2H, Ar), 6.86 (d, J 2.3 Hz, 2H, Ar), 6.74 (dd, J1 8.3 HzJ2 2.3 Hz, 2H, Ar), 5.94 (s, 1H, CH), 3.64 (s, 6H, CH3). 13C NMRspectrum (75.4 MHz, DMSO, δ, ppm): 153.8,140.7,131.4,130.1,127.4,126.6, 125.7, 124.4, 123.3, 120.2, 119.5, 118.7, 112.2, 111.6, 109.7, 101.9,55.8, 40.1. IR (KBr, cm-1): 3416 (NH); 3052 (C-H, Ar); 2993, 2936,2829 (C-H); 1624, 1582 (C]C Ar); 1512, 1482 (C]C, Ar and CH);1452, 1439 (OCH3); 1360, 1335, 1315 (C-N, Ar); 1211 (C-N); 797,773, 751, 715, 625 (C-H Ar). MS (APCI+, 20 V), m/z: 549 ([MH]).Anal. Calcd. for C37H29N3O2: C, 81.15; H, 5.34, N, 7.67; O, 5.84%;found C 81.22, H 5.33, N 7.62%.

References: [1]Dyes and Pigments,2017,vol. 139,p. 487 – 497.

10
[ 1006-94-6 ]
[ 1593-60-8 ]
5-methoxy-3-[(4-methylphenyl)sulfanyl]-1H-indole [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5284 – 5288.

11
[ 1006-94-6 ]
[ 105-45-3 ]
[ 621-63-6 ]
methyl 4-(5-methoxy-1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]

References: [1]Green Chemistry,2019,vol. 21,p. 2061 – 2069.

12
[ 1006-94-6 ]
[ 50606-58-1 ]
C₂₁H₂₄N₂O [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2019,vol. 180,p. 383 – 397.

13
[ 1006-94-6 ]
[ 3471-31-6 ]
5,5′-Dimethoxy-diindolylmethane [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4286 – 4293.

14
[ 1006-94-6 ]
[ 2150-46-1 ]
methyl 2-hydroxy-9-methoxy-6H-benzofuro[2,3-b]indole-1-carboxylate [ No CAS ]

References: [1]Green Chemistry,2021,vol. 23,p. 5031 – 5036.

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