(+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

Base Information

• Chemical Name: (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone
• CAS No.: 149524-36-7
• Molecular Formula: C₁₅H₁₃F₂N₃O₂
• Molecular Weight: 305.284
• Mol file: 149524-36-7.mol

Synonyms:(+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

Chemical Property of (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone

There total 9 articles about (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone 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:

(+/-)-5-(Azidomethyl)-3-<4-(3-pyridyl)-3,5-difluorophenyl>-2-oxazolidinone (149524-35-6) → (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (149524-36-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 16h; Yield given;

DOI:10.1021/jo00121a050

Reference yield:

3-Bromopyridine (626-55-1,163928-56-1) → (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (149524-36-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi, ZnCl₂ / 2.) Pd(PPh₃)4 / 1.) THF, hexane, -78 deg C, 4 h, 2.) THF, r.t. to reflux, 4 h

2: 1 N aq. HCl / 0.5 h

3: 87 percent / K₂CO₃ / tetrahydrofuran / 2 h / Ambient temperature

4: 96 percent / NaH, n-Bu₄NI / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h

5: 49 percent / pyridine, I₂ / CHCl₃ / 1.5 h / 50 °C

6: NaN₃ / dimethylformamide / 2 h / 55 °C

7: H₂ / 10percent Pd/C / methanol; ethyl acetate / 16 h

With pyridine; hydrogenchloride; n-butyllithium; sodium azide; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; zinc(II) chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a050

Reference yield:

3,5-difluoroaniline (372-39-4) → (+/-)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (149524-36-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 20 min, 2.) -70 deg C, 45 min

2: 1.) n-BuLi, ZnCl₂ / 2.) Pd(PPh₃)4 / 1.) THF, hexane, -78 deg C, 4 h, 2.) THF, r.t. to reflux, 4 h

3: 1 N aq. HCl / 0.5 h

4: 87 percent / K₂CO₃ / tetrahydrofuran / 2 h / Ambient temperature

5: 96 percent / NaH, n-Bu₄NI / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h

6: 49 percent / pyridine, I₂ / CHCl₃ / 1.5 h / 50 °C

7: NaN₃ / dimethylformamide / 2 h / 55 °C

8: H₂ / 10percent Pd/C / methanol; ethyl acetate / 16 h

With pyridine; hydrogenchloride; n-butyllithium; sodium azide; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; zinc(II) chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a050

upstream raw materials:

(+/-)-5-(Azidomethyl)-3-<4-(3-pyridyl)-3,5-difluorophenyl>-2-oxazolidinone

3-Bromopyridine

3,5-difluoroaniline

4-(3-Pyridyl)-3,5-difluoroaniline