O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

Base Information

Chemical Name:O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol
CAS No.:1384313-02-3
Molecular Formula:C₂₀H₃₀BClN₂O₆
Molecular Weight:440.732
Hs Code.:

Synonyms:O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

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Chemical Property of O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

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Technology Process of O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

There total 5 articles about O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol 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: 62.0%

: 1384312-89-3
O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-4-aminophenol

: 73183-34-3
bis(pinacol)diborane

: 1384313-02-3
O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

Guidance literature:: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 50 ℃; for 28h; regioselective reaction; Inert atmosphere;
DOI:10.1021/ja303443m

Reference yield: 62.0%

: 1384312-89-3
O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-4-aminophenol

: 73183-34-3
bis(pinacol)diborane

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 1384313-02-3
O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

Guidance literature:: With catalyst: (Ir(OMe)COD)2/4,4'-tBu₂-2,2'-bipyridine; In further solvent(s); protected aniline reacted with pinacolborane and B2(O2C2Me4)2 in tert-butyl methyl ether in the presence of Ir complex (2 mol.-%) and 4,4'-di-tert-butyl-2,2'-bipyridine (4 mol.-%) at 50°C; detd. by (1)H NMR spectroscopy;
DOI:10.1021/ja303443m

Reference yield:

: 911297-03-5
N-(3-chloro-4-hydroxyphenyl)carbamic acid tert-butyl ester

: 1384313-02-3
O-(N',N'-dimethylcarbamoyl)-N-(tert-butoxycarbonyl)-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-aminophenol

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 25 h / 70 °C / Inert atmosphere

2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 28 h / 50 °C / Inert atmosphere

With pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran;
DOI:10.1021/ja303443m