6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

Base Information

• Chemical Name: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide
• CAS No.: 1571111-64-2
• Molecular Formula: C₂₄H₂₃BF₃NO₃
• Molecular Weight: 441.258
• Mol file: 1571111-64-2.mol

Synonyms:6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

Chemical Property of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

There total 6 articles about 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide 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: 66.0%

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid (1290056-68-6) + 3-trifluoromethylaniline (98-16-8) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide (1571111-64-2)

Guidance literature:

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.25h;

3-trifluoromethylaniline; In dichloromethane; at 20 ℃;

DOI:10.1021/ml5000417

Reference yield:

6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester (255050-65-8) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide (1571111-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0.25 h / 0 °C

3.2: 20 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide monohydrate; water; potassium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/ml5000417

Reference yield:

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid methyl ester (919363-25-0) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide (1571111-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0.25 h / 0 °C

2.2: 20 °C

With dmap; lithium hydroxide monohydrate; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml5000417

upstream raw materials:

6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid methyl ester

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid

3-trifluoromethylaniline

Downstream raw materials:

6-(3-amino-1H-indazol-4-yl)-N-(3-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

Refernces

• 1、 Lv, Yongcong,Li, Mengyuan,Liu, Ting,Tong, Linjiang,Peng, Ting,Wei, Lixin,Ding, Jian,Xie, Hua,Duan, Wenhu. "Discovery of a new series of naphthamides as potent VEGFR-2 kinase inhibitors". . p. 592 - 597. Retrieved 2014/06/09.