tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
• CAS No.: 1218790-30-7
• Molecular Formula: C19H25BClNO4
• Molecular Weight: 377.676
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80682308
• Wikidata: Q82606628
• Mol file: 1218790-30-7.mol

Synonyms:1218790-30-7;tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate;1-BOC-5-chloroindole-3-boronic acid, pinacol ester;1-BOC-5-chloroindole-3-boronic acid pinacol ester;tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate;1-Boc-5-chloroindole-3-boronic acidpinacol ester;DTXSID80682308;MRVFRFXOZGTHHX-UHFFFAOYSA-N;MFCD15143612;AKOS015999329;DS-17491;FT-0760554;A891352;1-Boc-5-chloro-1H-indole-3-boronic acid pinacol ester;1H-Indole-1-carboxylic acid, 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester;tert-Butyl5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Chemical Property of tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Chemical Property:

• PSA: 49.69000
• LogP: 4.37710
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 377.1565161
• Heavy Atom Count: 26
• Complexity: 546

Purity/Quality:

97% ^*data from raw suppliers

1-BOC-5-chloroindole-3-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=CN(C3=C2C=C(C=C3)Cl)C(=O)OC(C)(C)C

Technology Process of tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

There total 5 articles about tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 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: 96.0%

tert-butyl 5-chloro-1H-indole-1-carboxylate (129822-48-6) + bis(pinacol)diborane (73183-34-3) → tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole-1-carboxylate (1218790-30-7)

Guidance literature:

With [iridium(I)(1,5-cyclooctadiene)(1,10-phenantroline)chloride]; In octane; at 80 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1021/om500420d

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-chloro-1H-indole (17422-32-1) + bis(pinacol)diborane (73183-34-3) → tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole-1-carboxylate (1218790-30-7)

Guidance literature:

di-tert-butyl dicarbonate; 5-chloro-1H-indole; With dmap; In tetrahydrofuran; at 23 ℃;

bis(pinacol)diborane; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; at 80 ℃;

DOI:10.1039/d1sc02838c

Reference yield: 84.0%

tert-butyl 5-chloro-3-iodo-1H-indole-1-carboxylate (1048039-49-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole-1-carboxylate (1218790-30-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In toluene; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2017.01.025

upstream raw materials:

tert-butyl 5-chloro-3-iodo-1H-indole-1-carboxylate

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

5-chloro-1H-indole

3-iodo-5-chloro-1H-indole