(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester
• CAS No.: 1168150-46-6
• Molecular Formula: C18H15NO4
• Molecular Weight: 309.321
• Mol file: 1168150-46-6.mol

Synonyms:(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester;BIBF1120 Intermediate4;Nintedanib ethanesulfonate intermediates;(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl este;methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

Chemical Property of (3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester

Chemical Property:

• Boiling Point: 523.8±50.0 °C(Predicted)
• PKA: 10.62±0.20(Predicted)
• PSA: 64.63000
• Density: 1.273±0.06 g/cm3(Predicted)
• LogP: 3.07800
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99.5%+ ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester

There total 8 articles about (3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester 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: 93.5%

(E)-1-cholroacetyl-3-(methoxy(phenyl)methylene)-2-indolone-6-methylformate (1174335-83-1) → (E)-methyl 3-(methoxy(phenyl)methylene)-2-indolone-6-carboxylic acid methyl ester (1168150-46-6)

Guidance literature:

With methanol; potassium hydroxide; for 0.666667h; Reflux;

Reference yield:

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (14192-26-8) → (E)-methyl 3-(methoxy(phenyl)methylene)-2-indolone-6-carboxylic acid methyl ester (1168150-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene / 4 h / Reflux

2.1: acetic anhydride / toluene / Reflux

2.2: 120 h / 20 - 104 °C

3.1: potassium hydroxide; methanol / 0.67 h / Reflux

With methanol; acetic anhydride; potassium hydroxide; In toluene;

Reference yield:

methyl 1-(2-chloroacetyl)-2-oxoindoline-6-carboxylate (1160293-25-3) → (E)-methyl 3-(methoxy(phenyl)methylene)-2-indolone-6-carboxylic acid methyl ester (1168150-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic anhydride / toluene / Reflux

1.2: 120 h / 20 - 104 °C

2.1: potassium hydroxide; methanol / 0.67 h / Reflux

With methanol; acetic anhydride; potassium hydroxide; In toluene;

upstream raw materials:

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

methyl 1-(2-chloroacetyl)-2-oxoindoline-6-carboxylate

(E)-1-cholroacetyl-3-(methoxy(phenyl)methylene)-2-indolone-6-methylformate

orthobenzoic acid trimethyl ester

Downstream raw materials:

nintedanib

Refernces

• 1、 -. "Indole ketone compound or its derivatives and their use". . . Retrieved 2017/02/02.