sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate

Base Information

• Chemical Name: sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate
• CAS No.: 1225441-51-9
• Molecular Formula: C₂₉H₂₂NO₁₁S*Na
• Molecular Weight: 615.55

Synonyms:sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate

Chemical Property of sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate

There total 25 articles about sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate 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: 61.0%

5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl 2,2,2-trichloroethyl sulfate (1225441-63-3) → sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate (1225441-51-9)

Guidance literature:

5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl 2,2,2-trichloroethyl sulfate; With ammonium formate; zinc; In tetrahydrofuran; methanol; at 20 ℃; for 2h;

In methanol;

DOI:10.3987/COM-09-S(S)100

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate (1225441-51-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: potassium carbonate / acetone / 9 h / Inert atmosphere; Reflux

2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C

2.3: pH 3

3.1: dichloromethane / 26 h / 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere

5.1: potassium hydroxide / ethanol; water / 2 h / Reflux

6.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux

7.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 1.5 h / -40 °C / Inert atmosphere

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 30 h / Reflux

10.1: hydrogenchloride / methanol / 19 h / 30 °C

11.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

12.1: boron trichloride / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

13.1: ammonium formate; zinc / tetrahydrofuran; methanol / 15 h / 20 °C

13.2: Amberlite IRC-50 (Na⁺ form)

With quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; tert.-butyl lithium; ammonium formate; pyridinium p-toluenesulfonate; boron trichloride; sodium carbonate; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; copper(II) oxide; potassium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; 4.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.bmc.2011.10.030

Reference yield:

1-benzyloxy-4-bromo-2-methoxy-5-(methoxymethoxy)benzene (1225441-54-2) → sodium 5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl sulfate (1225441-51-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C

1.3: pH 3

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere

3.1: hydrogenchloride / methanol / 3 h / 20 °C

4.1: toluene-4-sulfonic acid / dichloromethane / 3.5 h / Reflux

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere

6.1: potassium hydroxide / ethanol; water / 2 h / Reflux

7.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux

8.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere

9.1: boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 1.5 h / -40 °C / Inert atmosphere

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 30 h / Reflux

11.1: hydrogenchloride / methanol / 19 h / 30 °C

12.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

13.1: boron trichloride / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

14.1: ammonium formate; zinc / tetrahydrofuran; methanol / 15 h / 20 °C

14.2: Amberlite IRC-50 (Na⁺ form)

With quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; tert.-butyl lithium; ammonium formate; pyridinium p-toluenesulfonate; boron trichloride; sodium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; copper(II) oxide; potassium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 2.1: Suzuki-Miyaura coupling / 5.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.bmc.2011.10.030

upstream raw materials:

5-{3-hydroxy-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-14-yl}-2-methoxyphenyl 2,2,2-trichloroethyl sulfate

1-benzyloxy-4-bromo-2-methoxy-5-(methoxymethoxy)benzene

4-methoxy-3-(methoxymethoxy)phenylboronic acid

dimethyl 3-[4-benzyloxy-5-methoxy-2-(methoxymethoxy)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate

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