3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester

Base Information

• Chemical Name: 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester
• CAS No.: 245510-58-1
• Molecular Formula: C₂₈H₂₇Cl₂N₃O₆
• Molecular Weight: 572.445

Synonyms:3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester

Chemical Property of 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester

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Technology Process of 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester

There total 1 articles about 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl 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: 52.0%

(acetylamino-phenylcarbamoyl-methyl)-phosphonic acid dimethyl ester + 4,6-dichloro-3-formyl-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester → 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester (245510-58-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃; for 7h;

DOI:10.1002/(SICI)1521-4184(19998)332:8<271::AID-ARDP271>3.0.CO;2-X

Reference yield: 60.0%

3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester (245510-58-1) → 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid allyl ester (245510-59-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/(SICI)1521-4184(19998)332:8<271::AID-ARDP271>3.0.CO;2-X

Reference yield:

3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-indole-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester (245510-58-1) → 3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

2: 55 percent / dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

With dimedone; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1: Decarboxylation / 2: Hydrolysis;

DOI:10.1002/(SICI)1521-4184(19998)332:8<271::AID-ARDP271>3.0.CO;2-X

Downstream raw materials:

3-(2-acetylamino-2-phenylcarbamoyl-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid allyl ester

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