2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate

Base Information

• Chemical Name: 2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate
• CAS No.: 856702-64-2
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293

Synonyms:

Chemical Property of 2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate

Chemical Property:

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Technology Process of 2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate

There total 1 articles about 2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate 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:

2-bromo-pyridine (109-04-6) + N-boc-2-pyrroleboronic acid (135884-31-0) → 2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate (856702-64-2) + 2-(1H-pyrrol-2-yl)pyridine (17285-54-0)

Guidance literature:

With [(t-Bu)3PH]BF₄; palladium diacetate; sodium hydroxide; In butan-1-ol; at 80 ℃; for 2h; Overall yield = 96 %; Inert atmosphere; Glovebox;

DOI:10.1002/ejoc.201402915

Reference yield: 99.0%

2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate (856702-64-2) → 2-(1H-pyrrol-2-yl)pyridine (17285-54-0)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 0 - 20 ℃; for 24h;

DOI:10.1002/ejic.201500783

Reference yield:

2-(2'-pyridino)pyrrole-1-tert-butylcarboxylate (856702-64-2) → (S)-4-(1-(2-(pyridin-2-yl)-1H-pyrrol-1-yl)ethyl)benzonitrile + 4-(1-(2-(pyridin-2-yl)-1H-pyrrol-1-yl)ethyl)benzonitrile

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / water; dichloromethane / 15 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / Inert atmosphere; Schlenk technique; Cooling with ice

2.2: 5 h / 20 °C / Inert atmosphere; Schlenk technique

3.1: palladium on activated carbon; hydrogen / methanol; water / 4 h / Schlenk technique

4.1: nickel(II) bromide dimethoxyethane; (S)-4-(tert-butyl)-2-(3-methylpyridin-2-yl)-4,5-dihydrooxazole; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate / acetone / 64 h / 23 °C / Inert atmosphere; Schlenk technique; Irradiation

With hydrogenchloride; nickel(II) bromide dimethoxyethane; palladium on activated carbon; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; (S)-4-(tert-butyl)-2-(3-methylpyridin-2-yl)-4,5-dihydrooxazole; hydrogen; sodium hydride; caesium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/acs.orglett.9b03338

upstream raw materials:

2-bromo-pyridine

N-boc-2-pyrroleboronic acid

Downstream raw materials:

2-(1H-pyrrol-2-yl)pyridine

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