methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

Base Information

• Chemical Name: methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate
• CAS No.: 2093243-16-2
• Molecular Formula: C₁₇H₁₃NO₄
• Molecular Weight: 295.295
• Mol file: 2093243-16-2.mol

Synonyms:

Chemical Property of methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

Chemical Property:

• Melting Point: >215°C (dec.)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

(Z)-Methyl3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (Z)-Methyl 3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate is a useful intermediate for the preparation of nintedanib esylate. Nintedanib is a drug for the treatment of idiopathic pulmonary fibrosis.

Technology Process of methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

There total 2 articles about methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (14192-26-8) + benzyl chloride (100-44-7) → methyl 3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (2093243-16-2)

Guidance literature:

With SMO-powder; In isopropyl alcohol; at -10 - -5 ℃; for 5h;

Reference yield: 61.0%

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (14192-26-8) + benzoyl chloride (98-88-4) → methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (2093243-16-2)

Guidance literature:

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; With sodium methylate; In isopropyl alcohol; for 0.25h;

benzoyl chloride; In isopropyl alcohol; at -10 - -5 ℃; for 5h; Reagent/catalyst; Solvent;

DOI:10.1080/00397911.2017.1297459

Reference yield:

methyl 3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (2093243-16-2) → methyl 1-acetyl-3-(((4-(2-chloro-N-methylacetamido)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1.5 h / 0 - 80 °C

2: methanol; N,N-dimethyl-formamide / 12 h / 60 - 65 °C

With pyridine; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester

benzyl chloride

benzoyl chloride

Refernces

• 1、 -. "POLYMORPH OF NINTEDANIB ETHANESULPHONATE, PROCESSES AND INTERMEDIATES THEREOF". Page/Page column 25; 26. . Retrieved 2016/11/21.