N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide

Base Information

• Chemical Name: N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide
• CAS No.: 146141-10-8
• Molecular Formula: C16H17FN2O
• Molecular Weight: 272.322
• DSSTox Substance ID: DTXSID20453978
• Nikkaji Number: J566.237K
• Wikidata: Q82275289
• Mol file: 146141-10-8.mol

Synonyms:N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide;146141-10-8;N-[2-(3-FLUOROPYRIDIN-2-YL)PHENYL]-2,2-DIMETHYLPROPANAMIDE;SCHEMBL1358968;DTXSID20453978;OVBPZKHZXQJCKW-UHFFFAOYSA-N;2,2-Dimethyl-N-[2-(3-fluoro-2-pyridinyl)phenyl]propanamide;n-[2-(3-fluoro -pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide;n-[2-(3-fluoro-pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide

Chemical Property of N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 272.13249133
• Heavy Atom Count: 20
• Complexity: 340

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)NC1=CC=CC=C1C2=C(C=CC=N2)F

Technology Process of N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide

There total 8 articles about N-(2-(3-fluoropyridin-2-yl)phenyl)pivalamide 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: 76.0%

3-fluoro-2-iodopyridine (146141-04-0) + 2-pivaloylaminophenyl boronic acid (146140-95-6) → N-[2-(3-fluoropyridin-2-yl)phenyl]-2,2-dimethylpropionamide (146141-10-8)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; for 48h; Heating;

DOI:10.1016/S0040-4020(01)80505-6

Reference yield:

2-chloro-3-fluoropyridine (17282-04-1) + 2-pivaloylaminophenyl boronic acid (146140-95-6) → N-[2-(3-fluoropyridin-2-yl)phenyl]-2,2-dimethylpropionamide (146141-10-8)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 20 - 83 ℃;

Reference yield:

3-fluoro-4-iodopyridine (22282-75-3) → N-[2-(3-fluoropyridin-2-yl)phenyl]-2,2-dimethylpropionamide (146141-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LDA, H₂O / tetrahydrofuran / 1.) -75 deg C, 1.5 h, 2.) -75 deg C, 2 h

2: 1.) 2 M K₂CO₃ / 2.) Pd(PPh₃)4 / 1.) ethanol, toluene, 0.5 h, 2.) reflux, 24 h

With water; potassium carbonate; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1021/jo00079a031

upstream raw materials:

3-fluoro-2-iodopyridine

2-pivaloylaminophenyl boronic acid

3-fluoro-4-iodopyridine

3-Fluoropyridine

Downstream raw materials:

4-bromo-2-(3-fluoropyridin-2-yl)-6-nitrophenylamine

2-(3-fluoropyridin-2-yl)-6-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

C₂₀H₁₉FN₆O₃

C₁₆H₁₁FN₄O₃