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

Base Information

Chemical Name:N-(3-bromophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthalenecarboxamide
CAS No.:1571111-74-4
Molecular Formula:C₂₃H₂₃BBrNO₃
Molecular Weight:452.156
Hs Code.:

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

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

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

There total 6 articles about N-(3-bromophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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: 63.0%

: 1290056-68-6
6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid

: 591-19-5
m-Bromoaniline

: 1571111-74-4
N-(3-bromophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthalenecarboxamide

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;

m-Bromoaniline; In dichloromethane; at 20 ℃;
DOI:10.1021/ml5000417

Reference yield:

: 255050-65-8
6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester

: 1571111-74-4
N-(3-bromophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthalenecarboxamide

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:

: 919363-25-0
6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid methyl ester

: 1571111-74-4
N-(3-bromophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthalenecarboxamide

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