1256584-75-4

Basic information

• Product Name: tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate
• Synonyms: tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate;tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate-10;6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate;2-Methyl-2-propanyl 6-cyano-2-[2-(4-ethyl-3-iodophenyl)-2-propany l]-1H-indole-3-carboxylate
• CAS NO: 1256584-75-4
• Molecular Formula: C25H27IN2O2
• Molecular Weight: 514.39855
• Mol File: 1256584-75-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 609.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• PKA: 14.00±0.30(Predicted)
• CAS DataBase Reference: tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate(1256584-75-4)
• EPA Substance Registry System: tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate(1256584-75-4)

Safety Data

• Hazardous Substances Data: 1256584-75-4(Hazardous Substances Data)

Usage

Description

tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate is a complex organic compound that serves as a crucial intermediate in the synthesis of Alectinib (C183360), a highly selective and potent anaplastic lymphoma kinase (ALK) inhibitor. tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate plays a significant role in the development of pharmaceuticals targeting specific cancer-related mutations.

Uses

Used in Pharmaceutical Industry:
tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate is used as a key intermediate in the synthesis of Alectinib, a medication designed to inhibit the activity of anaplastic lymphoma kinase (ALK). tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate is particularly effective against the resistant gatekeeper mutant, which contributes to reduced cell growth in cancer treatment. Its role in the development of Alectinib highlights its importance in creating targeted therapies for cancer patients.

Upstream product

• 100-41-4 ethylbenzene 
• 698394-60-4 2-bromo-1-(4-ethylphenyl)-2-methyl-propan-1-one 
• 698394-59-1 methyl 2-(4-ethylphenyl)-2-methyl-propanoate 
• 1247119-83-0 2-(4-ethylphenyl)-2-methyl-propanoic acid 
• 1256584-73-2 2-(4-ethyl-3-iodophenyl)-2-methylpropanoic acid 
• 40052-13-9 mono-tert-butyl malonate 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 1256584-74-3 tert-butyl 4-(4-ethyl-3-iodo-phenyl)-4-methyl-3-oxo-pentanoate 

Downstream Products

• 1256580-46-7 C⁽²⁴⁸⁾H₅₄₀₂ 

Relevant articles and documents

Preparation method of alectinib

The invention provides a preparation method of alectinib. The method comprises the following steps: taking 3-(4-ethylphenyl)-3-methylbutane-2-one as an initial raw material, carrying out an iodinationreaction on the initial raw material and an iodination reagent, and reacting obtained 3-(3-iodo-4-ethylphenyl)-2-methylbutane-2-one with a carbonylation reagent; carrying out a substitution reactionon obtained 4-(3-iodo-4-ethylphenyl)-4-methyl-3-oxovalerate and 4-chloro-3-nitro-benzonitrile in an alkaline environment, carrying out a reduction condensation reaction on obtained 4-(3-iodo-4-ethylphenyl)-2-(2-nitro-4-cyanophenyl)-4-methyl-3-oxovalerate, carrying out a cyclization reaction on obtained 6-cyano-2-(2-(4-ethyl-3-iodophenyl)prop-2-yl)-1H-methyl indole-3-carboxylate, and carrying out asubstitution reaction on obtained 9-ethyl-8-iodo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile and 4-(4-piperidyl)morpholine to obtain a finished product, namely the alectinib.The preparation method of alectinib has the main beneficial effects that the raw materials are cheap and are easy to obtain, the synthetic route is simple, the synthetic process is green and environmentally friendly, and industrial production is facilitated.

IMPROVED PROCESS FOR THE PREPARATION OF 9-ETHYL-6,6-DIMETHYL-8-[4-(MORPHOLIN-4-YL) PIPERIDIN-1-YL]-11-OXO-6,11-DIHYDRO-5H-BENZO[B]CARBAZOLE-3-CARBONITRILE HYDROCHLORIDE

The present invention relates to novel process for the preparation of 9-ethyl-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloride compound of formula-1a, represented by the following structural formula: The present invention also provides an improved process for the preparation of tert-butyl-4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoate having the following structural formula which is useful in the preparation of Alectinib and its pharmaceutical acceptable salts.