3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

Base Information

Chemical Name:3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene
CAS No.:1083414-72-5
Molecular Formula:C₂₄H₃₉BN₂O₆
Molecular Weight:462.394
Hs Code.:

Synonyms:3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

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Chemical Property of 3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

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Technology Process of 3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

There total 7 articles about 3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene 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: 80.0%

: 73183-34-3
bis(pinacol)diborane

: 3,5-bis[(N-tert-butoxycarbonyl)aminomethyl]-1-iodobenzene

: 1083414-72-5
3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

Guidance literature:: bis(pinacol)diborane; 3,5-bis[(N-tert-butoxycarbonyl)aminomethyl]-1-iodobenzene; With potassium acetate; for 1h; Inert atmosphere;

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dimethyl sulfoxide; at 80 ℃; for 18h; Inert atmosphere;
DOI:10.1002/anie.201200447

Reference yield: 79.0%

: 73183-34-3
bis(pinacol)diborane

: [3-Bromo-5-(tert-butoxycarbonylamino-methyl)-benzyl]-carbamic acid tert-butyl ester

: 1083414-72-5
3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 16h; Schlenk technique; Inert atmosphere;
DOI:10.1039/c5nj00759c

Reference yield:

: 1380485-22-2
1,3-bis(azidomethyl)-5-iodobenzene

: 1083414-72-5
3,5-bis[(tert-butoxycarbonyl)aminomethyl]-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzene

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine / tetrahydrofuran; water; N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

3.1: potassium acetate / 1 h / Inert atmosphere

3.2: 18 h / 80 °C / Inert atmosphere

With potassium acetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; 3.2: Suzuki-Miyaura cross coupling;
DOI:10.1002/anie.201200447