2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate

Base Information

• Chemical Name: 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate
• CAS No.: 413578-27-5
• Molecular Formula: C₃₂H₃₂N₂O₈S
• Molecular Weight: 604.681
• Mol file: 413578-27-5.mol

Synonyms:2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate

Chemical Property of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate

There total 20 articles about 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate 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: 100.0%

2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (413578-26-4) + methanesulfonyl chloride (124-63-0) → 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (413578-27-5)

Guidance literature:

With triethylamine; In dichloromethane; for 1h;

DOI:10.1021/jo060501o

Reference yield:

ethyl (4-amino-2-nitronaphthalen-1-yl)acetate (413577-69-2) → 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (413578-27-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. H₂SO₄ / 20 °C

1.2: aq. NaNO₂ / 0.08 h / 3 °C

1.3: 42 percent / aq. CuNO₃; Cu₂O / 3 h / 10 °C

2.1: K₂CO₃ / acetone / 20 °C

3.1: DIBAL-H / tetrahydrofuran / 0.25 h / 0 °C

4.1: 0.21 g / pyridine / 20 °C

5.1: H₂ / PtO₂ / tetrahydrofuran / 1 h / 20 °C / 2844.31 Torr

6.1: 37 percent / 1-hydroxybenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; pyridine / 120 h / 20 - 60 °C

7.1: K₂CO₃ / methanol / 20 °C

8.1: Et₃N / CH₂Cl₂ / cooling

With pyridine; sulfuric acid; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/jm050179u

Reference yield:

ethyl (4-hydroxy-2-nitronaphthalen-1-yl)acetate (413578-20-8) → 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (413578-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃ / acetone / 20 °C

2: DIBAL-H / tetrahydrofuran / 0.25 h / 0 °C

3: 0.21 g / pyridine / 20 °C

4: H₂ / PtO₂ / tetrahydrofuran / 1 h / 20 °C / 2844.31 Torr

5: 37 percent / 1-hydroxybenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; pyridine / 120 h / 20 - 60 °C

6: K₂CO₃ / methanol / 20 °C

7: Et₃N / CH₂Cl₂ / cooling

With pyridine; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/jm050179u

upstream raw materials:

2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol

methanesulfonyl chloride

2-[4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]ethanol

[4-acetoxy-2-ethoxycarbonylnaphthalen-1-yl]acetic acid

Downstream raw materials:

[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride