1000068-23-4

Basic information

• Product Name: 1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid
• Synonyms: 1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid
• CAS NO: 1000068-23-4
• Molecular Formula: C₁₄H₁₈BNO₅
• Molecular Weight: 291.10742
• Mol File: 1000068-23-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid(1000068-23-4)
• EPA Substance Registry System: 1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid(1000068-23-4)

Safety Data

• Hazardous Substances Data: 1000068-23-4(Hazardous Substances Data)

Usage

General Description

1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-ylboronic acid is a chemical compound most commonly used in synthetic chemistry as a reagent for palladium-catalyzed cross-coupling reactions, specifically Suzuki-Miyaura reactions. It is characterized by the presence of an indole ring, a boronic acid group, a methoxy group, and a tert-butoxycarbonyl (Boc) protecting group. The Boc group is used to protect an amine group during reaction conditions, while the boronic acid and methoxy groups contribute to its reactivity. As such, this compound often plays a role in the synthesis of complex organic molecules, especially pharmaceuticals and bioactive molecules.

InChI:InChI=1S/C14H18BNO5/c1-14(2,3)21-13(17)16-10-6-5-7-11(20-4)9(10)8-12(16)15(18)19/h5-8,18-19H,1-4H3

Upstream product

• 1269629-13-1 C₂₀H₃₀BNO₅ 
• 1093759-59-1 4-methoxyindole-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4837-90-5 4-methoxy-1H-indole 
• 5419-55-6 Triisopropyl borate 
• 4837-88-1 6-methoxy-2-nitrotoluene 
• 1443151-84-5 1-[(E)-2-(2-methoxy-6-nitrophenyl)vinyl]pyrrolidine 

Downstream Products

• 1187841-23-1 dimethyl 2-(2-((1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-yl)methyl)benzylidene)malonate 
• 1028386-71-1 (2-cyclopent-1-enyl-4-methoxy-1H-indole) 

Relevant articles and documents

1,3,5-TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF

The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH2 or a group -NHSO2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use

Trisoxazoline/Cu(II)-catalyzed asymmetric intramolecular Friedel-Crafts alkylation reaction of indoles

Intramolecular Friedel-Crafts alkylation reaction of indoles catalyzed by trisoxazoline/copper(II) is described. This annulation provides an easy access to polycyclic indole derivatives with up to 90% ee in up to 99% yield.