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

Base Information

• Chemical Name: [4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride
• CAS No.: 413578-28-6
• Molecular Formula: C₃₁H₂₉ClN₂O₅
• Molecular Weight: 545.035
• Mol file: 413578-28-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about [4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride 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: 81.0%

2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (413578-27-5) → [4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (413578-28-6)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

DOI:10.1021/jo060501o

Reference yield:

ethyl (4-hydroxy-2-nitronaphthalen-1-yl)acetate (413578-20-8) → [4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (413578-28-6)

Guidance literature:

Multi-step reaction with 8 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

8: 75 mg / LiCl / dimethylformamide / 72 h / 20 °C

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

DOI:10.1021/jm050179u

Reference yield:

ethyl (4-amino-2-nitronaphthalen-1-yl)acetate (413577-69-2) → [4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (413578-28-6)

Guidance literature:

Multi-step reaction with 9 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

9.1: 75 mg / LiCl / dimethylformamide / 72 h / 20 °C

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

DOI:10.1021/jm050179u

upstream raw materials:

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

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

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

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