5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Base Information

• Chemical Name: 5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 1219637-79-2
• Molecular Formula: C15H20BNO3
• Molecular Weight: 273.1352
• Mol file: 1219637-79-2.mol

Synonyms:5-Methoxy-1H-indole-7-boronic acid pinacol ester;5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property of 5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property:

• PSA: 43.48000
• Density: 1.13
• LogP: 2.47570

Purity/Quality:

98%Min ^*data from raw suppliers

5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

There total 5 articles about 5-Methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 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: 60.0%

5-methoxylindole (1006-94-6) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole (1219637-79-2)

Guidance literature:

With diethylsilane or dimethylchlorosilane/N(CH₂CH₃)3; catalyst: (Ir(C₈H₁₂)Cl)2/(NC₅H₄C(CH₃)3-4)2; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In tetrahydrofuran; react. indole deriv. with silane in toluene at room temp. in the presence of Ru complex, evapn., addn. of boron compds., Ir complex and 4,4'-di-tert-butylbipyridine in THF, react. at 80°C; workup with 3 M aq. sodium acetate;

DOI:10.1021/ja1006405

Reference yield: 36.0%

5-methoxylindole (1006-94-6) + bis(pinacol)diborane (73183-34-3) → 5-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole (1219637-79-2)

Guidance literature:

5-methoxylindole; With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; H₂SiEt₂; In toluene; at 20 ℃; for 18h; Sealed tube;

bis(pinacol)diborane; 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; toluene; at 80 ℃; for 22h;

With sodium acetate; In tetrahydrofuran; water; toluene; at 20 ℃; for 4h;

DOI:10.1021/jo4006987

Reference yield:

C19H30BNO3Si → 5-methoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole (1219637-79-2)

Guidance literature:

With water; sodium acetate; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja1006405

upstream raw materials:

5-methoxylindole

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane