3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione

Base Information

• Chemical Name: 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione
• CAS No.: 130966-39-1
• Molecular Formula: C₁₈H₁₆N₄O₃
• Molecular Weight: 336.35
• Mol file: 130966-39-1.mol

Synonyms:3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione

Chemical Property of 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione

There total 10 articles about 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione 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: 68.0%

3-(2-Azido-ethyl)-1-benzyl-4,6,7-trimethoxy-1H-indole (130966-38-0) → 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione (130966-39-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile;

DOI:10.1246/cl.1990.1591

Reference yield:

5-nitroveratral (22027-96-9) → 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione (130966-39-1)

Guidance literature:

Multi-step reaction with 10 steps

1: Fe, conc. HCl / methanol / Heating

2: pyridine

3: Baeyer-Villiger oxidation

4: K₂CO₃ / methanol

5: 98 percent / BH₃*SMe₂ / tetrahydrofuran / Heating

6: 80 percent / ethanol / Heating

7: LiAlH₄ / tetrahydrofuran / Ambient temperature

8: NEt₃ / CH₂Cl₂ / 0 °C

9: NaN₃ / dimethylformamide / 60 °C

10: 68 percent / CAN / acetonitrile; H₂O

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; ammonium cerium(IV) nitrate; dimethylsulfide borane complex; iron; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1990.1591

Reference yield:

3-amino-4,5-dimethoxy-benzaldehyde → 3-(2-Azido-ethyl)-1-benzyl-6-methoxy-1H-indole-4,7-dione (130966-39-1)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine

2: Baeyer-Villiger oxidation

3: K₂CO₃ / methanol

4: 98 percent / BH₃*SMe₂ / tetrahydrofuran / Heating

5: 80 percent / ethanol / Heating

6: LiAlH₄ / tetrahydrofuran / Ambient temperature

7: NEt₃ / CH₂Cl₂ / 0 °C

8: NaN₃ / dimethylformamide / 60 °C

9: 68 percent / CAN / acetonitrile; H₂O

With pyridine; lithium aluminium tetrahydride; sodium azide; ammonium cerium(IV) nitrate; dimethylsulfide borane complex; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1990.1591

upstream raw materials:

3-(2-Azido-ethyl)-1-benzyl-4,6,7-trimethoxy-1H-indole

5-nitroveratral

Benzyl-(2,3,5-trimethoxy-phenyl)-amine

N-(2,3,5-Trimethoxy-phenyl)-benzamide

Downstream raw materials:

3-(2-Azido-ethyl)-1-benzyl-6-[2-(3,5-dibromo-4-hydroxy-phenyl)-ethylamino]-1H-indole-4,7-dione