140640-09-1

Basic information

• Product Name: 1H-Indole-7-carboxaldehyde, 3-methyl- (9CI)
• Synonyms: 1H-Indole-7-carboxaldehyde, 3-methyl- (9CI);1H-Indole-7-carboxaldehyde, 3-Methyl-
• CAS NO: 140640-09-1
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• Product Categories: ALDEHYDE
• Mol File: 140640-09-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-7-carboxaldehyde, 3-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-7-carboxaldehyde, 3-methyl- (9CI)(140640-09-1)
• EPA Substance Registry System: 1H-Indole-7-carboxaldehyde, 3-methyl- (9CI)(140640-09-1)

Safety Data

• Hazardous Substances Data: 140640-09-1(Hazardous Substances Data)

Usage

Structure

A derivative of indole with a methyl group at the 3-position and a carboxaldehyde group at the 7-position

Type of compound

Heterocyclic aromatic compound

Usage

Commonly used in organic synthesis, particularly in the preparation of various pharmaceuticals and other biologically active compounds

Reactivity

Unique structure and reactivity make it a valuable building block for the synthesis of complex organic molecules

Applications

Potential applications in the field of medicinal chemistry and drug discovery

Safety

Should be handled with caution as it may have harmful effects if not used properly.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 242805-87-4 1-(2,2-diethylbutanoyl)-3-methylindole 
• 83-34-1 3-Methylindole 
• 552-89-6 2-nitro-benzaldehyde 
• 1074-88-0 1H-indole-7-carbaldehyde 
• 1174005-78-7 3-formyl-1H-indole-7-carbaldehyde 

Relevant articles and documents

Organocatalytic asymmetric cascade reactions of 7-vinylindoles: Diastereo- And enantioselective synthesis of c7-functionalized indoles

The first catalytic asymmetric cascade reaction of 7-vinylindoles has been established by the rational design of such substrates. Cascade reactions with isatin-derived 3-indolylmethanols in the presence of a chiral phosphoric acid derivative allow the diastereo- and enantioselective synthesis of C7-functionalized indoles as well as the construction of cyclopenta[b]indole and spirooxindole frameworks (all > 95:5 d.r., 94- > 99% ee). This approach not only addresses the great challenge of the catalytic asymmetric synthesis of C7-functionalized indoles, but also provides an efficient method for constructing biologically important cyclopenta-[b]indole and spirooxindole scaffolds with excellent optical purity. Investigation of the reaction pathway and activation mode has suggested that this cascade reaction proceeds through a vinylogous Michael addition/Friedel-Crafts process, in which dual H-bonding activation of the two reactants plays a crucial role.

Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Hetero-triarylmethanes from Racemic Indolyl Alcohols

The direct enantioselective 1,4- and 1,8-arylations of 7-methide-7H-indoles and 6-methide-6H-indoles, respectively, generated in situ from diarylmethanols, with electron-rich arenes as nucleophiles, has been achieved in the presence of chiral phosphoric acids (CPAs). These two remote activation protocols provide an efficient approach for the construction of diverse hetero-triarylmethanes in high yields (up to 97 %) and with excellent enantioselectivities (up to 96 %). Mechanistically inspired experiments tentatively indicate that the catalytic enantioselective 1,4-addition as well as the formal SN1 substitution could proceed efficiently in the similar catalytic systems. Furthermore, the modification of the catalytic system and diarylmethanol structure successfully deviates the reactivity toward a remote, highly enantioselective 1,8-arylation reaction. This flexible activation mode and novel reactivity of diarylmethanols expand the synthetic potential of chiral phosphoric acids.

Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region

A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome.

Directed C-7 lithiation of 1-(2,2-diethylbutanoyl)indoles

Directed lithiation of 1-acylindole derivatives was investigated. It was discovered that a bulky 2,2-diethylbutanoyl (DEB) group could promote unusual C-7 lithiation. Especially in the case of 3-substituted 1-(DEB)indoles, selective C-7 lithiation was achieved in a synthetically useful level. The DEB group was readily removed by H2O/tert-BuOK/THF system after functionalization at C-7. This, therefore, allows easy generation of 3,7- disubstituted indole derivatives which are not readily available by conventional methodologies.

Certain indole derivatives useful as leukotriene antagonists

A compound of the formula STR1 in which R1 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehydo, --CH2 Z, --CH=CH--Z or --CH2 CH2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or --CONR7 R8 where R7 and R8 are each hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen, C1-4 alkyl, optionally substituted phenyl, or C1-4 alkyl substituted by --CONR7 R8 or an optionally protected acid group; R5 is STR2 where W is --CH=CH--, --CH=N--, --N=CH--, --O-- or --S--, R9 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1-4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is --O--(CH2)n CR11 R12, --CR11 R12 --, --CR11 R12.(CH2)n.CR13 R14 -- or --CR11 =CR12 -- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR15 R16 --, --CR15 =CR16 -- or --CR15 R16.CR17 R18 -- where R15, R16, R17 and R18 are each hydrogen or C 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

N-Benzyl-Indoles, processes for their preparation and pharmaceutical compositions containing them

A compound of the formula in which R1 is hydrogen, halo, C??? alkyl, C??? alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C??? alkyl, aldehydo,-CH?Z,-CH=CH-Z or-CH?CH?Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or-CONR?R? where R? and R? are each hydrogen or C??? alkyl, R3 and R? are each hydrogen, C??? alkyl, optionally substituted phenyl, or C??? alkyl substituted by-CONR?R? or an optionally protected acid group; R? is where W is-CH=CH-,-CH=N-,-N=CH-,-O-or-S-, R? is hydrogen, halo, C??? alkyl, C? ?? alkoxy or trihalomethyl, and R1? is hydrogen, C? ?? alkyl, C??? alkenyl, C??? cycloalkyl or C??? alkyl-C??? cycloalkyl; R? is hydrogen or C??? alkyl; X is-O-(CH?)nCR11CR12-,-CR11R12-,-CR11R12.(CH?) n.CR13R1?-or-CR11=CR12-where R11, R12, R13 and R1? are each hydrogen or C??? alkyl, and n is 0, 1 or 2; and Y is-O-CR1?R1?-,-CR1?=CR1?-or-CR1? R1?.CR1?R1?-where R1?, R1?, R1? and R1? are each hydrogen or C??? alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.