(9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Base Information

• Chemical Name: (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate
• CAS No.: 1579291-57-8
• Molecular Formula: C₁₇H₂₂N₄O₂
• Molecular Weight: 314.387
• Mol file: 1579291-57-8.mol

Synonyms:(9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Chemical Property of (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

There total 5 articles about (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate 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: 85.0%

2-azido-4-methylphenylboronic acid pinacolate ester (1579291-80-7) + 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) → (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1579291-57-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; water; at 80 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo500252e

Reference yield:

2-bromo-5-methylaniline (53078-85-6) → (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1579291-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere

2: 2-Methyl-2-nitropropane; trimethylsilylazide / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / water; tetrahydrofuran / 1.5 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2-Methyl-2-nitropropane; trimethylsilylazide; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 3: |Suzuki Coupling;

DOI:10.1021/jo500252e

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1579291-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

2: tetrahydrofuran / 15 h / -78 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / water; tetrahydrofuran / 1.5 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; lithium hexamethyldisilazane; In tetrahydrofuran; water; 3: |Suzuki Coupling;

DOI:10.1021/jo500252e

upstream raw materials:

2-azido-4-methylphenylboronic acid pinacolate ester

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

2-bromo-5-methylaniline

N-tert-butyloxycarbonylpiperidin-4-one