944418-90-0

Basic information

• Product Name: 1H-indole, 4-methoxy-2-phenyl-
• CAS NO: 944418-90-0
• Molecular Weight: 223.274
• Mol File: 944418-90-0.mol

Chemical Properties

• CAS DataBase Reference: 1H-indole, 4-methoxy-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-indole, 4-methoxy-2-phenyl-(944418-90-0)
• EPA Substance Registry System: 1H-indole, 4-methoxy-2-phenyl-(944418-90-0)

Safety Data

• Hazardous Substances Data: 944418-90-0(Hazardous Substances Data)

Usage

General Description

1H-indole, 4-methoxy-2-phenyl- is a chemical compound with the molecular formula C16H13NO. It is a derivative of indole, and is often used in the production of pharmaceuticals and agrochemicals. The compound has a complex aromatic structure, with a methoxy group and a phenyl group attached to the indole ring. It has been found to have various biological activities and is used in research and drug development for its potential therapeutic applications. Additionally, it is also used as a key intermediate in the synthesis of other organic compounds. Overall, 1H-indole, 4-methoxy-2-phenyl- plays a significant role in the field of medicinal chemistry and organic synthesis.

Upstream product

• 536-74-3 phenylacetylene 
• 945470-20-2 1-benzyl-4-methoxy-2-phenyl-1H-indole 
• 4837-90-5 4-methoxy-1H-indole 
• 98-80-6 phenylboronic acid 
• 536-90-3 m-Anisidine 
• 1159883-21-2 C₈H₉FO 
• 100-47-0 benzonitrile 
• 76064-14-7 N-(3-methoxy-2-methylphenyl)benzamide 
• 98-88-4 benzoyl chloride 
• 108-86-1 bromobenzene 
• 945470-14-4 1-bromo-3-methoxy-2-phenylethynylbenzene 
• 945470-07-5 3-chloro-2-phenylethynylanisole 
• 98-86-2 acetophenone 
• 28203-05-6 dimethoxy-2,2 phenyl-2 ethanol-1 

Downstream Products

• 72338-95-5 2-phenyl-4-hydroxy-indole 

Relevant articles and documents

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles

Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition-metal-free assembly of 2-aryl indoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.

Synthetic method of 2-substituted indoles compounds

The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.

Pyridylmethylamine–Palladium Catalytic Systems: A Selective Alternative in the C?H Arylation of Indole

A highly efficient pyridylmethylamine-Pd alternative catalytic system for the C?H arylation of indole was explored. Variously substituted aryl groups were regio- and chemoselectively installed at the indole nucleus by using barium hydroxide as the base. The method was found to be efficient even in the presence of hindered coupling partners and Pd-reactive bonds.

Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement

In situ generation of the reactive amphoteric α-amino aldehyde with simple α-hydroxy ketones and phenylamine via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.

New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer

We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.

Multi-site cyclization via initial C-H activation using a rhodium(III) catalyst: Rapid assembly of frameworks containing indoles and indolines

Tandem multi-site cyclization triggered by Rh(III)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.

"on water" direct and site-selective Pd-catalysed C-H arylation of (NH)-indoles

This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [Pd(OAc)2/dppm] that works "on water" giving site-selective C-H arylation of (NH)-indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the "extra-catalytic" base/halide partners. These innovative methodologies allow a high-yielding access to both C2 and C3-arylindoles, as well as 2,3-diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties. Copyright

Regioselective synthesis of 4- and 7-alkoxyindoles from 2,3-dihalophenols: Application to the preparation of indole inhibitors of phospholipase A 2

(Chemical Equation Presented) An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commercially available starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followed by two pallad

Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2- bromotrifluoroacetanilides

(Chemical Equation Presented) Cross-coupling of 1-alkynes with vinyl iodides occurs at 80°C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 °C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables me reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.