6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid

Base Information

• Chemical Name: 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid
• CAS No.: 1279707-80-0
• Molecular Formula: C₂₇H₂₁N₃O₄
• Molecular Weight: 451.481
• Mol file: 1279707-80-0.mol

Synonyms:6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid

Chemical Property of 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid

There total 17 articles about 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-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: 3.0%

6-(1-benzyl-5-methoxy-1H-indol-3-yl)-7-methoxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester (1279707-79-7) → 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid (1279707-80-0)

Guidance literature:

6-(1-benzyl-5-methoxy-1H-indol-3-yl)-7-methoxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester; With boron tribromide; In dichloromethane; for 2h; Inert atmosphere; Reflux;

With hydrogenchloride; In dichloromethane; water; Cooling with ice;

DOI:10.1016/j.tet.2011.01.029

Reference yield:

1-(toluene-4-sulfonyl)-1H-indol-5-ol → 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid (1279707-80-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: propionic acid / toluene / 24 h / Reflux

2.1: water; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C

5.1: methanol; potassium hydroxide / tetrahydrofuran / 0.5 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: methanol; potassium hydroxide / tetrahydrofuran / 3 h / Reflux

7.2: 20 °C

8.1: acetic acid / 2 h / 80 °C / Inert atmosphere

8.2: 20 °C / pH 10 / Cooling with ice

8.3: pH 3

9.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

10.1: hydrogenchloride / methanol; water / 24 h / Reflux

10.2: 20 °C

11.1: boron tribromide / dichloromethane / 2 h / Inert atmosphere; Reflux

11.2: Cooling with ice

With hydrogenchloride; methanol; water; dihydrogen peroxide; boron tribromide; potassium carbonate; acetic acid; propionic acid; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2011.01.029

Reference yield:

indol-5-ol (1953-54-4) → 6-[1-benzyl-5-hydroxy-1H-indol-3-yl]-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid (1279707-80-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux

3.2: 20 °C

4.1: propionic acid / toluene / 24 h / Reflux

5.1: water; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C

8.1: methanol; potassium hydroxide / tetrahydrofuran / 0.5 h / 20 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

10.1: methanol; potassium hydroxide / tetrahydrofuran / 3 h / Reflux

10.2: 20 °C

11.1: acetic acid / 2 h / 80 °C / Inert atmosphere

11.2: 20 °C / pH 10 / Cooling with ice

11.3: pH 3

12.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

13.1: hydrogenchloride / methanol; water / 24 h / Reflux

13.2: 20 °C

14.1: boron tribromide / dichloromethane / 2 h / Inert atmosphere; Reflux

14.2: Cooling with ice

With 1H-imidazole; hydrogenchloride; methanol; water; dihydrogen peroxide; boron tribromide; sodium hydride; potassium carbonate; acetic acid; propionic acid; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1016/j.tet.2011.01.029

upstream raw materials:

indol-5-ol

5-(tert-butyl-dimethyl-silanyloxy)-1H-indole

(1-benzyl-5-methoxy-1H-indol-3-yl)-[5-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-methanone

(1-benzyl-5-methoxy-1H-indol-3-yl)-(5-methoxy-1H-indol-4-yl)-methanone

Refernces