(E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: (E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid
• CAS No.: 161230-88-2
• Molecular Formula: C₁₈H₁₁Cl₂NO₄
• Molecular Weight: 376.196
• UNII: PP86UX2L28
• DSSTox Substance ID: DTXSID101017669
• Nikkaji Number: J775.441H
• ChEMBL ID: CHEMBL180427
• Mol file: 161230-88-2.mol

Synonyms:3-(2-phenyl-2-carboxyethenyl)-4,6-dichloro-1H-indole-2-carboxylic acid;MDL 105,519;MDL 105519;MDL-105519

Chemical Property of (E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid

Chemical Property:

• Boiling Point: 601.3±55.0 °C(Predicted)
• PKA: 3.20±0.19(Predicted)
• PSA: 90.39000
• Density: 1.594±0.06 g/cm3(Predicted)
• LogP: 4.79810
• Solubility.: DMSO: 5 mg/mL
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 375.0065132
• Heavy Atom Count: 25
• Complexity: 561

Purity/Quality:

97% ^*data from raw suppliers

MDL 105,519 ≥98% (HPLC), solid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=CC2=C(NC3=C2C(=CC(=C3)Cl)Cl)C(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C(=C\C2=C(NC3=C2C(=CC(=C3)Cl)Cl)C(=O)O)/C(=O)O

Technology Process of (E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid

There total 6 articles about (E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-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:

(E)-3-(2-carboxy-2-phenylvinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179105-90-9) → (E)-4,6-dichloro-3-(2-phenyl-2-carboxyethenyl)indole-2-carboxylic acid (161230-88-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 7.5h; Heating;

DOI:10.1021/jm0491849

Reference yield:

4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-92-4) → (E)-4,6-dichloro-3-(2-phenyl-2-carboxyethenyl)indole-2-carboxylic acid (161230-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C

1.2: 53 percent / tetrahydrofuran / 2 h / -78 - 20 °C

2.1: 36.3 percent / K₂CO₃; Pd(PPh₃)4 / toluene / 1 h / 90 °C

3.1: 98 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

4.1: aq. LiOH / tetrahydrofuran / 7.5 h / Heating

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 1.2: Horner-Emmons reaction / 2.1: Suzuki-Miyaura reaction;

DOI:10.1021/jm0491849

Reference yield:

(Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-70-8) → (E)-4,6-dichloro-3-(2-phenyl-2-carboxyethenyl)indole-2-carboxylic acid (161230-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 36.3 percent / K₂CO₃; Pd(PPh₃)4 / toluene / 1 h / 90 °C

2: 98 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

3: aq. LiOH / tetrahydrofuran / 7.5 h / Heating

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; 1: Suzuki-Miyaura reaction;

DOI:10.1021/jm0491849

upstream raw materials:

(E)-3-(2-carboxy-2-phenylvinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

(Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

(E)-3-(2-(tert-butoxycarbonyl)-2-phenylvinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

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