6-Chloro-2-oxoindoline-5-carboxylic acid

Base Information

• Chemical Name: 6-Chloro-2-oxoindoline-5-carboxylic acid
• CAS No.: 1156390-49-6
• Molecular Formula: C9H6ClNO3
• Molecular Weight: 211.6
• European Community (EC) Number: 844-663-1
• Mol file: 1156390-49-6.mol

Synonyms:6-Chloro-2-oxoindoline-5-carboxylic acid;1156390-49-6;6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid;6-chloro-2-oxo-1,3-dihydroindole-5-carboxylic acid;6-Chloro-2,3-dihydro-2-oxo-1H-indole-5-carboxylic Acid;SCHEMBL2720180;AMY26942;MFCD12174764;AKOS009493140;SB18289;6-Chloro-2-oxoindoline-5-carboxylicacid;BS-13971;CS-0132071;EN300-93183;O11572;Z425365102

Chemical Property of 6-Chloro-2-oxoindoline-5-carboxylic acid

Chemical Property:

• Boiling Point: 452.1±45.0 °C(Predicted)
• PKA: 2.94±0.20(Predicted)
• PSA: 66.40000
• Density: 1.561±0.06 g/cm3(Predicted)
• LogP: 1.67080
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 211.0036207
• Heavy Atom Count: 14
• Complexity: 281

Purity/Quality:

97% ^*data from raw suppliers

6-Chloro-2,3-dihydro-2-oxo-1H-indole-5-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC(=C(C=C2NC1=O)Cl)C(=O)O
• Uses: 6-Chloro-2,3-dihydro-2-oxo-1H-indole-5-carboxylic Acid is an intermediate used in the synthesis of EPZ031686, the first orally bioavailable small molecule SMYD3 inhibitor.

Technology Process of 6-Chloro-2-oxoindoline-5-carboxylic acid

There total 2 articles about 6-Chloro-2-oxoindoline-5-carboxylic acid 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:

6-chloro-5-(2-chloroacetyl) indolin-2-one (118307-04-3) → 6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (1156390-49-6)

Guidance literature:

6-chloro-5-(2-chloroacetyl) indolin-2-one; With pyridine; at 90 ℃; for 3h;

With sodium hydroxide; In water; at 100 ℃; for 3h;

DOI:10.1016/j.bmc.2017.04.047

Reference yield:

6-chloro-2-oxindole (56341-37-8) → 6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (1156390-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 4 h / 20 °C

2.1: pyridine / 3 h / 90 °C

2.2: 3 h / 100 °C

With pyridine; aluminum (III) chloride; In 1,2-dichloro-ethane;

DOI:10.1016/j.bmc.2017.04.047

Reference yield: 8.0%

6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (1156390-49-6) + (1R,3S,5S)-8-([[1-(4,4,4-trifluorobutyl)piperidin-4-yl]methane]sulfonyl)-8-azabicyclo[3.2.1]octan-3-amine → EPZ031686 (1808011-22-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 10 ℃; for 12h;

DOI:10.1021/acsmedchemlett.5b00272

upstream raw materials:

6-chloro-2-oxindole

6-chloro-5-(2-chloroacetyl) indolin-2-one

Downstream raw materials:

EPZ031686