6H-Pyrrolo[3,4-b]pyridine-6-acetic acid, 3-(chloromethyl)-4-(2,4-dichlorophenyl)-5,7-dihydro-2-methyl-5-oxo-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: 6H-Pyrrolo[3,4-b]pyridine-6-acetic acid, 3-(chloromethyl)-4-(2,4-dichlorophenyl)-5,7-dihydro-2-methyl-5-oxo-, 1,1-dimethylethyl ester
• CAS No.: 915731-62-3
• Molecular Formula: C21H21Cl3N2O3
• Molecular Weight: 455.768

Synonyms:

Chemical Property of 6H-Pyrrolo[3,4-b]pyridine-6-acetic acid, 3-(chloromethyl)-4-(2,4-dichlorophenyl)-5,7-dihydro-2-methyl-5-oxo-, 1,1-dimethylethyl ester

Chemical Property:

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Technology Process of 6H-Pyrrolo[3,4-b]pyridine-6-acetic acid, 3-(chloromethyl)-4-(2,4-dichlorophenyl)-5,7-dihydro-2-methyl-5-oxo-, 1,1-dimethylethyl ester

There total 9 articles about 6H-Pyrrolo[3,4-b]pyridine-6-acetic acid, 3-(chloromethyl)-4-(2,4-dichlorophenyl)-5,7-dihydro-2-methyl-5-oxo-, 1,1-dimethylethyl 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:

6-(2-tert-butoxy-2-oxoethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid (915297-05-1) → (R)-tert-Butyl 2-(3-(chloromethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)acetate (915731-62-3)

Guidance literature:

Multi-step reaction with 3 steps

1: trichloroacetonitrile / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.42 h / 0 °C / Inert atmosphere

3: triethylamine; methanesulfonyl chloride / dichloromethane / Inert atmosphere

With methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; trichloroacetonitrile; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm4008906

Reference yield:

(Z)-ethyl 4-chloro-2-(2,4-dichlorobenzylidene)-3-oxobutanoate (915296-79-6) → (R)-tert-Butyl 2-(3-(chloromethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)acetate (915731-62-3)

Guidance literature:

Multi-step reaction with 7 steps

1: isopropyl alcohol / 18 h / 20 °C / Inert atmosphere

2: acetic acid; nitric acid / water / 18 h / 20 °C / Inert atmosphere

3: ethanol / 150 °C / Microwave irradiation; Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / Inert atmosphere

5: triethylamine / tetrahydrofuran / Inert atmosphere

6: sodium tetrahydroborate / water; tetrahydrofuran / Inert atmosphere

7: triethylamine; methanesulfonyl chloride / dichloromethane / Inert atmosphere

With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; nitric acid; acetic acid; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; isopropyl alcohol;

DOI:10.1021/jm4008906

Reference yield:

benzyl 6-(2-tert-butoxy-2-oxoethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate (915297-04-0) → (R)-tert-Butyl 2-(3-(chloromethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)acetate (915731-62-3)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / Inert atmosphere

2: triethylamine / tetrahydrofuran / Inert atmosphere

3: sodium tetrahydroborate / water; tetrahydrofuran / Inert atmosphere

4: triethylamine; methanesulfonyl chloride / dichloromethane / Inert atmosphere

With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm4008906

upstream raw materials:

tert-butyl 2-(3-(chlorocarbonyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)acetate

(Z)-ethyl 4-chloro-2-(2,4-dichlorobenzylidene)-3-oxobutanoate

benzyl 6-(2-tert-butoxy-2-oxoethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate

6-(2-tert-butoxy-2-oxoethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid

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