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Chemistry
Organic Building Blocks
Indoles
4-methoxy-1H-indole
4,5,6-Trimethoxy-1H-indole
Chemistry
Organic Building Blocks
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4-methoxy-1H-indole

[ CAS No. 30448-04-5 ] {[proInfo.proName]}

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Chemical Structure| 30448-04-5
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Product Details of [ 30448-04-5 ]

CAS No. :30448-04-5 MDL No. :MFCD00049062
Formula : C11H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 207.23 Pubchem ID :-
Synonyms :

Safety of [ 30448-04-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 30448-04-5 ]

* 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.

  • Downstream synthetic route of [ 30448-04-5 ]

[ 30448-04-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 590417-55-3 ]
  • [ 30448-04-5 ]
  • [ 1334752-51-0 ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate; copper(II) oxide In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux; 4.1.1. 4,5,6-Trimethoxy-1'-methyl-1’H-[1,4']biindolyl (13) To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%); mp 107-108 °C; 1H NMR (500 MHz, CDCl3) δ 3.75 (s, 3H), 3.86 (s, 3H), 3.91 (s, 3H), 4.17 (s, 3H), 6.39 (d, J = 3.0 Hz, 1H), 6.67 (s, 1H), 6.75 (d, J = 3.0 Hz, 1H), 7.08 (d, J = 3.0 Hz, 1H), 7.21 (dd, J = 1.0, 7.0 Hz, 1H), 7.30 (d, J = 3.0 Hz, 1H), 7.33 (dd, J = 7.0, 8.0 Hz, 1H), 7.37 (d, J = 8.0, 1H). MS (EI) m/z: 336 (M+, 100%), 321 (78%). HRMS-EI for C20H20N2O3 (M+): calcd, 336.1474; found, 336.1474; 13C NMR (100 MHz, DMSO): δ 32.7, 55.8, 60.4, 60.8, 89.6, 98.3, 100.2, 109.0, 115.2, 115.3, 121.5, 123.4, 127.1, 130.4, 131.0, 132.5, 135.4, 137.9, 145.2, 150.5.
Reference： [1]Location in patent: experimental part Lai, Mei-Jung; Chang, Jang-Yang; Lee, Hsueh-Yun; Kuo, Ching-Chuan; Lin, Mei-Hsiang; Hsieh, Hsing-Pang; Chang, Chi-Yen; Wu, Jian-Sung; Wu, Su-Ying; Shey, Kuang-Shing; Liou, Jing-Ping [European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3623 - 3629]
  • 2
  • [ 23145-07-5 ]
  • [ 30448-04-5 ]
  • [ 1334752-53-2 ]
YieldReaction ConditionsOperation in experiment
6.4% With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 3
  • [ 4964-71-0 ]
  • [ 30448-04-5 ]
  • [ 1334752-56-5 ]
YieldReaction ConditionsOperation in experiment
43% With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30percent)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 4
  • [ 13676-02-3 ]
  • [ 30448-04-5 ]
  • [ 1334752-54-3 ]
YieldReaction ConditionsOperation in experiment
43% With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 5
  • [ 848841-54-3 ]
  • [ 30448-04-5 ]
  • [ 1334752-58-7 ]
YieldReaction ConditionsOperation in experiment
22% With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 6
  • [ 30448-04-5 ]
  • [ 52692-09-8 ]
  • C18H18N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 7
  • [ 30448-04-5 ]
  • [ 52692-09-8 ]
  • [ 1334752-47-4 ]
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629
  • 8
  • [ 30448-04-5 ]
  • [ 3964-04-3 ]
  • [ 1334752-55-4 ]
YieldReaction ConditionsOperation in experiment
64% With caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred mixture of 21 (0.25 g, 1.21 mmol), 4-bromo-1-methylindole (0.31 g, 1.45 mmol), cesium carbonate (0.79 g, 2.41 mmol) and copper oxide (0.01 g, 0.12 mmol) in DMF (2 mL) was refluxed for 24 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, concentrated under reduced pressure and purified by silica gel flash column chromatography (EtOAc : n-hexane = 1 : 3) to afford compound 13 as a pale white solid (0.12 g, 30%)
Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3623 - 3629

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4-methoxy-1H-indole
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4-methoxy-1H-indole

Technical Information

• Acetal Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Grignard Reagents Transform Esters into Alcohols • Nomenclature of Ethers • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Ethers • Ring Opening of Oxacyclopropane • Synthesis of Alcohols from Tertiary Ethers • The Nucleophilic Opening of Oxacyclopropanes
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