Pharmaceutical Intermediate - 5-Fluoro-2-oxindole

Chemical Properties

Name: 5-fluorindole-2-ketone

Synonyms: 5-fluoro-1, 3-dihydroindole-2-one; Indole 5-fluoro oxide; 5-fluorindolone; 5-fluorindolone; Indole 5-fluoro oxide

CAS: 56341-41-4

Molecular weight: 151.13

PSA: 29.10000

LogP: 1.45830

Molecular formula：

Appearance: light yellow crystal

Density: 1.311 g/cm3

Melting point: 143-147 °C(lit.)

Boiling point: 307.2ºC at 760 mmHg

Flash: DHS 139.6 C

Refractive index: 1.56

Uses

As an intermediate

5- fluorindole-2 - ketone is a useful intermediate of sunitinib and its derivatives. Sunitinib is the first of a new class of drugs that selectively target multiple receptor tyrosine kinases. The drug is mainly used to treat metastatic or advanced renal cell carcinoma, gastrointestinal stromal tumor and advanced pancreatic neuroendocrine carcinoma. Approved by the US Food and Drug Administration (FDA) on January 26, 2006, the company achieved sales of $1.187 billion in 2011.

As a reagent

As a reagent, it is used as reactant for preparation of:

Glycogen synthase kinase 3 beta (GSK-3β) inhibitors

Antitumor agents

Cyclooxygenase 1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) inhibitors

Multitargeted Receptor Tyrosine Kinase Inhibitors

Non-peptide thrombopoietin (TPO) receptor ligands

Aurora kinase inhibitors

Inhibitors of cyclin-dependent kinase CDK2/cyclin A

Selective norepinephrine reuptake inhibitors

B-cell lymphoma-extra large molecule (Bcl-XL) inhibitor Z36

Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1)

Preparation

5- fluorindole-2 - one is an organic ketone, which can be used as an intermediate in the preparation of Sunitinib. First, 4-fluoroaniline was used as the starting material to react with chloral hydrate and hydroxylamine hydrochloride to form p-fluoroisonitroacetanilide. Then, 5-fluorindole-2-one was formed by cyclization under the action of concentrated sulfuric acid. Finally, 5-fluoroindole-2-one was obtained by the reaction of Wolff-Kishner-Huangming long with a total yield of 66%.

Shanghai QiXin New Materials Technology Co.,Ltd was established in 2016, is located in Shanghai China, is dedicated to the development of new materials, high-tech R & D process optimization and drug intermediates and reagent.  It has won the national key support of new and high technology enterprises, in the whole management system introduced the ERP system and OA office system, from raw materials procurement - receiving inspection - production - finished goods inspection to control sales management and so on each link, technical support at the same time, there is a strong technical force, advanced detection instruments good perfect management system to control the quality of the products, To ensure the requirements of mass production.