(2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone

Base Information

• Chemical Name: (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone
• CAS No.: 115017-13-5
• Molecular Formula: C₁₃H₁₀F₂N₂O
• Molecular Weight: 248.232
• Mol file: 115017-13-5.mol

Synonyms:(2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone

Chemical Property of (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone

There total 8 articles about (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone 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-4,6-difluoroaniline (444-14-4) → (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone (115017-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / CHCl₃ / 1.) RT, 15 min, 2.) reflux, 3 h, 3.) RT, overnight

2: 1.) 2.4 M n-butyllithium / 1.) a.) THF, hexane, -100 deg C, 15 min, b.) from -100 deg C to 0 deg C, 2.) -78 deg C, 30 min

3: 1.) pyridinium chlorochromate, 2.) 70percent aq. sulfuric acid / 1.) methylene dichloride, RT, overnight, 2.) from 95 to 100 deg C, overnight

With n-butyllithium; sulfuric acid; pyridinium chlorochromate; In chloroform;

DOI:10.1021/jo00250a019

Reference yield:

3,5-Lutidine (591-22-0) → (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone (115017-13-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 27 percent / potassium permanganate / H₂O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight

2: 73 percent / hydrogen chloride / Heating

3: 80 percent / LAH / diethyl ether / 0.5 h / -78 °C

4: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene dichloride, -60 deg C, 20 min, 2.) from -60 deg C to RT

5: 1.) 2.4 M n-butyllithium / 1.) a.) THF, hexane, -100 deg C, 15 min, b.) from -100 deg C to 0 deg C, 2.) -78 deg C, 30 min

6: 1.) pyridinium chlorochromate, 2.) 70percent aq. sulfuric acid / 1.) methylene dichloride, RT, overnight, 2.) from 95 to 100 deg C, overnight

With hydrogenchloride; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In diethyl ether; water;

DOI:10.1021/jo00250a019

Reference yield:

5-methylnicotinic acid (3222-49-9) → (2-Amino-3,5-difluoro-phenyl)-(5-methyl-pyridin-3-yl)-methanone (115017-13-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / hydrogen chloride / Heating

2: 80 percent / LAH / diethyl ether / 0.5 h / -78 °C

3: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene dichloride, -60 deg C, 20 min, 2.) from -60 deg C to RT

4: 1.) 2.4 M n-butyllithium / 1.) a.) THF, hexane, -100 deg C, 15 min, b.) from -100 deg C to 0 deg C, 2.) -78 deg C, 30 min

5: 1.) pyridinium chlorochromate, 2.) 70percent aq. sulfuric acid / 1.) methylene dichloride, RT, overnight, 2.) from 95 to 100 deg C, overnight

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In diethyl ether;

DOI:10.1021/jo00250a019

upstream raw materials:

3,5-Lutidine

5-methylnicotinic acid

(5-methylpyridin-3-yl)methanol

5-methyl-3-pyridinecarboxaldehyde

Refernces