3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine

Base Information

• Chemical Name: 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine
• CAS No.: 1584233-71-5
• Molecular Formula: C₁₆H₁₄N₄O₂
• Molecular Weight: 294.313
• Mol file: 1584233-71-5.mol

Synonyms:3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine

Chemical Property of 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine

There total 3 articles about 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine 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: 83.0%

3-Bromopyridine (626-55-1,163928-56-1) + 1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazole (400877-60-3) → 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine (1584233-71-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; Trimethylacetic acid; In N,N-dimethyl-formamide; at 120 ℃; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/jo4025418

Reference yield: 80.0%

3-(tosyloxy)pyridine (67284-17-7) + 1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazole (400877-60-3) → 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine (1584233-71-5)

Guidance literature:

With palladium diacetate; caesium carbonate; cesium pivalate; XPhos; In toluene; at 120 ℃; for 16h; Sealed tube; Glovebox;

DOI:10.1021/acs.joc.7b00550

Reference yield:

4-Methylbenzyl bromide (104-81-4) → 3-{1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazol-5-yl}pyridine (1584233-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 90 °C / Inert atmosphere; Schlenk technique

2: potassium carbonate; copper(l) iodide; Trimethylacetic acid; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 120 °C / Schlenk technique; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; Trimethylacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo4025418

upstream raw materials:

3-Bromopyridine

1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazole

4-Methylbenzyl bromide

3-(tosyloxy)pyridine