9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

Base Information

Chemical Name:9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid
CAS No.:1428796-82-0
Molecular Formula:C₂₂H₂₀FNO₃
Molecular Weight:365.404
Hs Code.:

Synonyms:9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

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Chemical Property of 9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

Chemical Property:

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Technology Process of 9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

There total 12 articles about 9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-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:

: 90151-40-9
4-amino-3-methoxybenzaldehyde

: 1428796-82-0
9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-Butyl nitrite; copper(I) bromide / acetonitrile / 18 h / 20 °C

2.1: ammonium acetate; acetic acid / 18 h / 80 °C

3.1: sodium tetrahydroborate; borane-THF / tetrahydrofuran / 18 h / 0 - 65 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: trichlorophosphate / toluene / 2 h / 110 °C

6.1: potassium carbonate; triethylamine / acetonitrile / 2 h / 100 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 18.5 h / 90 °C / Inert atmosphere; Sealed tube

8.1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / Inert atmosphere

9.1: palladium diacetate; caesium carbonate; triphenylphosphine / 1,4-dioxane / 41.25 h / 90 - 100 °C / Inert atmosphere; Sealed tube

10.1: water; sodium hydroxide / ethanol / 3 h / 80 °C

10.2: pH Ca_. 4

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; n-Butyl nitrite; palladium 10% on activated carbon; ammonium acetate; water; hydrogen; palladium diacetate; potassium carbonate; caesium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(I) bromide; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene; acetonitrile;

Reference yield:

: 1428796-81-9
ethyl 9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylate

: 1428796-82-0
9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

Guidance literature:: ethyl 9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylate; With water; sodium hydroxide; In ethanol; at 80 ℃; for 3h;

With hydrogenchloride; In water; pH=Ca. 4;

Reference yield:

: 704-13-2
5-formyl-2-nitrophenol

: 1428796-82-0
9-ethyl-3-(3-fluorophenyl)-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C

2.1: iron; ammonium chloride / ethanol; water / 2 h / 78 °C

3.1: n-Butyl nitrite; copper(I) bromide / acetonitrile / 18 h / 20 °C

4.1: ammonium acetate; acetic acid / 18 h / 80 °C

5.1: sodium tetrahydroborate; borane-THF / tetrahydrofuran / 18 h / 0 - 65 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.1: trichlorophosphate / toluene / 2 h / 110 °C

8.1: potassium carbonate; triethylamine / acetonitrile / 2 h / 100 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 18.5 h / 90 °C / Inert atmosphere; Sealed tube

10.1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / Inert atmosphere

11.1: palladium diacetate; caesium carbonate; triphenylphosphine / 1,4-dioxane / 41.25 h / 90 - 100 °C / Inert atmosphere; Sealed tube

12.1: water; sodium hydroxide / ethanol / 3 h / 80 °C

12.2: pH Ca_. 4

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; n-Butyl nitrite; palladium 10% on activated carbon; ammonium acetate; water; hydrogen; palladium diacetate; iron; potassium carbonate; ammonium chloride; caesium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(I) bromide; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;