1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4 -methylphenyl)sulfonyl]-, ethyl ester

Base Information

Chemical Name:1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4 -methylphenyl)sulfonyl]-, ethyl ester
CAS No.:179105-94-3
Molecular Formula:C29H26Cl2N2O5S
Molecular Weight:585.508
Hs Code.:

1H-Indole-2-carboxylic acid,
4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4
-methylphenyl)sulfonyl]-, ethyl ester

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Chemical Property of 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4 -methylphenyl)sulfonyl]-, ethyl ester

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Technology Process of 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4 -methylphenyl)sulfonyl]-, ethyl ester

There total 6 articles about 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1E)-3-(dimethylamino)-3-oxo-2-phenyl-1-propenyl]-1-[(4 -methylphenyl)sulfonyl]-, ethyl 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: 88.0%

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

: 124-40-3
dimethyl amine

: 179105-94-3
4,6-dichloro-3-(2-dimethylcarbamoyl-2-phenyl-vinyl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Guidance literature:: With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/jm0491849

Reference yield:

: 179106-92-4
4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

: 179105-94-3
4,6-dichloro-3-(2-dimethylcarbamoyl-2-phenyl-vinyl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

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: 88 percent / 1-hydroxybenzotriazole hydrate; 1-(3-(dimethylamino)propyl)-3-ethylcarbidiimide*HCl / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 1.2: Horner-Emmons reaction / 2.1: Suzuki-Miyaura reaction;
DOI:10.1021/jm0491849

Reference yield:

: 179106-70-8
(Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

: 179105-94-3
4,6-dichloro-3-(2-dimethylcarbamoyl-2-phenyl-vinyl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

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: 88 percent / 1-hydroxybenzotriazole hydrate; 1-(3-(dimethylamino)propyl)-3-ethylcarbidiimide*HCl / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; toluene; 1: Suzuki-Miyaura reaction;
DOI:10.1021/jm0491849