5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole

Base Information

• Chemical Name: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole
• CAS No.: 1192037-87-8
• Molecular Formula: C₁₅H₁₉BBrNO₂
• Molecular Weight: 336.036
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80681952
• Wikidata: Q82606144
• Mol file: 1192037-87-8.mol

Synonyms:1192037-87-8;5-BROMO-1-METHYL-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE;5-Bromo-1-methylindole-2-boronic acid, pinacol ester;5-bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole;5-Bromo-1-methylindole-2-boronic acid,pinacol ester;C15H19BBrNO2;DTXSID80681952;MFCD12923192;AKOS015999319;MB12097;BS-19497;CS-0174880;F87004;A892626

Chemical Property of 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole

Chemical Property:

• PSA: 23.39000
• LogP: 3.24000
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 335.06922
• Heavy Atom Count: 20
• Complexity: 374

Purity/Quality:

98%min ^*data from raw suppliers

5-Bromo-1-methylindole-2-boronicAcid,PinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(N2C)C=CC(=C3)Br
• Uses: 5-Bromo-1-methylindole-2-boronic Acid, Pinacol Ester is used in iridium N-heterocyclic carbene-catalyzed carbon-hydrogen borylation of arenes by diisopropylaminoborane.

Technology Process of 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole

There total 4 articles about 5-Bromo-1-methyl-2-(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: 72.0%

bis(pinacol)diborane (73183-34-3) + 5-bromo-1,2-dimethyl-1H-indole → 5-bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1192037-87-8) + 2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane (94242-85-0)

Guidance literature:

bis(pinacol)diborane; 5-bromo-1,2-dimethyl-1H-indole; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

Reference yield: 71.0%

5-bromo-1-methyl-H-indole (10075-52-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1192037-87-8)

Guidance literature:

5-bromo-1-methyl-H-indole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With benzoic acid; In hexane; at 180 ℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;

With hydrogenchloride; In hexane; water; for 0.5h; regioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c00809

Reference yield: 65.0%

5-bromo-1-methyl-H-indole (10075-52-2) + bis(pinacol)diborane (73183-34-3) → 5-bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1192037-87-8)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; octane; at 140 ℃; for 16h; regioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201808590

upstream raw materials:

5-bromo-1-methyl-H-indole

2,3-dimethyl-2,3-butane diol

diisopropopylaminoborane

bis(pinacol)diborane

Refernces

• 1、 Tobisu, Mamoru,Igarashi, Takuya,Chatani, Naoto. "Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane". . p. 654 - 661. Retrieved 2016.
• 2、 Chen, Quan,Jiang, Jiachen,Wang, Li,Wu, Aizhen,Yin, Youzhi,Zhang, Hua,Zhang, Ke,Zhao, Mengzhen,Zhong, Qi,Zou, Youliang. "Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation". . p. 15104 - 15109. Retrieved 2021/12/09.