2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole

Base Information

• Chemical Name: 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole
• CAS No.: 1380597-28-3
• Molecular Formula: C₃₆H₂₈N₄O₂
• Molecular Weight: 548.644

Synonyms:2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole

Chemical Property of 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole

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Technology Process of 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole

There total 2 articles about 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole 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: 91.0%

3-(1-benzylaziridin-2-yl)-1,5-bis(6-methoxynaphthalen-2-yl)penta-1,4-diyn-3-ol (1380597-18-1) → 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole (1380597-28-3)

Guidance literature:

3-(1-benzylaziridin-2-yl)-1,5-bis(6-methoxynaphthalen-2-yl)penta-1,4-diyn-3-ol; With N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide; In acetonitrile; at 20 ℃; Inert atmosphere;

With silver(I) acetate; In acetonitrile; for 0.5h; Inert atmosphere;

DOI:10.1021/ol301187s

Reference yield:

2-ethynyl-6-methoxynaphthalene (129113-00-4) → 2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole (1380597-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / Inert atmosphere

2.1: N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide / acetonitrile / 20 °C / Inert atmosphere

2.2: 0.5 h / Inert atmosphere

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; trimethylsilylazide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/ol301187s

Reference yield: 78.0%

2-(azidomethyl)-1-benzyl-5-(6-methoxynaphthalen-2-yl)-3-((6-methoxynaphthalen-2-yl)ethynyl)-1H-pyrrole (1380597-28-3) → 1-benzyl-2,5-bis(6-methoxynaphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine (1380597-40-9)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 140 ℃; Inert atmosphere;

DOI:10.1021/ol301187s

upstream raw materials:

3-(1-benzylaziridin-2-yl)-1,5-bis(6-methoxynaphthalen-2-yl)penta-1,4-diyn-3-ol

2-ethynyl-6-methoxynaphthalene

Downstream raw materials:

1-benzyl-2,5-bis(6-methoxynaphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine

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