Industrial Consultancy & Sponsored Research (IC&SR) , IIT Madras
Recoverable and Reusable Palladium Nanoparticle Catalyzed Stereoselective One-pot Synthesis of 3-arylidene-2-oxindoles
Categories for this Invention
Technology: Recoverable and Reusable Palladium Nanoparticle
Category: Chemistry & Chemical Analysis
Industry: Pharmaceutical,Chemical
Application: Medicinal, material, and natural product synthesis
Market: The global market size was valued at USD 209.85 billion in 2019 and is poised to grow from USD 222.4 billion in 2023 to USD 352.98 billion by 2031, growing at a CAGR of 5.9% in the forecast period (2024-2031).
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Problem Statement
- Oxindoles are organic compounds found in mammals’ body fluids and tissues, and natural products of plants.
- Used in traditional medicine for various ailments including infection, cancer, gastric ulcers, arthritis, and mild physical inflammations.
- Nintedanib, an oxindole derivative, is approved to treat interstitial lung ailments like idiopathic pulmonary fibrosis and chronic fibrosis.
- Other oxindole derivatives include Sunitinib and Semaxanib, targeting angiogenesis colon-rectal cancer.
- Synthesis of oxindole derivatives is of great interest due to their wide-ranging biological importance.
- 3-arylidene-2-oxindoles show better biological activity than unsubstituted oxindoles.
- Previous synthetic methods have major problems, such as the use of homogeneous Pd-catalyst, expensive transition metal catalyst, and the need for Cu as an external oxidant.
Technology
A process for preparing a compound of formula (VII)
- the process comprising:
 a) reacting a compound of formula (I) - with compound of formula (II)
- in presence of palladium-binaphthyl nanoparticles (Pd-BNP) and base in presence of solvent to obtain a reaction mixture,
- b) treating alcoholic solution of secondary amine (IIIa)
- with the reaction mixture obtained from step (a) to obtain a compound of formula (VII);
- wherein ‘R’ is independently selected from a group comprising hydrogen, alkyl group, aryl group, acetyl group;
- ‘R1’ is independently selected from a group comprising hydrogen and alkoxy group;
- ‘R2’ is hydrogen;‘R3’ is cyclohexyl;
- alternatively, ‘R2’ and ‘R3’ are connected to form
Key Features / Value Proposition
Selection
- Alkyl, alkoxy, n-alkyl, aryl, and secondary amine are selected from various groups.
Secondary amine
- The alcoholic solution of secondary amine is either methanolic or ethanolic.
- Secondary amine is selected from morpholine, piperidine, pyrrolidine, 4-methylpipridine, and cyclohexanamine.
Solvent
- The solvent used in step (a) is tetrahydrofuran, cyclic ether, ethanol, methanol, 1,4-dioxane, toluene, and combinations thereof.
Temperature
- The process is carried out at room temperature and step (b) at a temperature range of 50℃ to 90℃, preferably around 70℃.
Time
- The process is carried out for 4 hours to 8 hours, preferably 6 hours, and 1 hours to 3 hours, preferably 2 hours
Base
- Sodium ethoxide, sodium methoxide,dimethylamine,diisopropylamine,diisopropylethylamine, triethylamine, and potassium carbonate.
- The process includes isolation and/or purification of the corresponding product.
Recoverable, reusable
- Synthesize oxindole derivatives using recoverable, reusable heterogeneous palladium catalysts.
- Develop a method for synthesizing oxindole derivatives using a transition metal catalyst.
Applications
- Avoid external oxidant use of copper and metal impurity in final product.
- Crucial due to widespread applications in medicinal, material, and natural product synthesis.
Questions about this Technology?
Contact For Licensing
sm-marketing@imail.iitm.ac.in
ipoffice2@iitm.ac.in
Research Lab
Prof. Govindasamy Sekar
Department. of Chemistry
Intellectual Property
IITM IDF Ref. 2328
Patent No: IN 547590
Technology Readiness Level
TRL- 3
Experimental Proof of concept