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

Base Information

• Chemical Name: tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
• CAS No.: 1256359-99-5
• Molecular Formula: C₂₀H₂₈BNO₅
• Molecular Weight: 373.257
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID90682319
• Nikkaji Number: J3.518.036B
• Wikidata: Q82606642
• Mol file: 1256359-99-5.mol

Synonyms:1256359-99-5;tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate;1-Boc-5-Methoxyindole-3-boronic acid, pinacol ester;tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate;1-Boc-5-Methoxyindole-3-boronic acid pinacol ester;SCHEMBL1356725;DTXSID90682319;MFCD16295115;AKOS015999333;AS-43910;CS-0173856;J3.518.036B;1H-Indole-1-carboxylic acid, 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-5-methoxy-1H-indole-1-carboxylic acid tert-butyl ester;tert-Butyl5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

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

Chemical Property:

• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 373.2060532
• Heavy Atom Count: 27
• Complexity: 557

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-5-Methoxyindole-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)OC)C(=O)OC(C)(C)C

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

There total 6 articles about tert-Butyl 5-methoxy-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: 80.0%

1-(tert-butyloxycarbonyl)-5-methoxyindole (99275-47-5) + bis(pinacol)diborane (73183-34-3) → tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate (1256359-99-5)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; for 0.0166667h; Inert atmosphere;

1-(tert-butyloxycarbonyl)-5-methoxyindole; In tetrahydrofuran; at 70 ℃; for 72h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2015.09.033

Reference yield: 33.0%

→ tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate (1256359-99-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In diethylene glycol dimethyl ether; at 80 ℃; Inert atmosphere; Sealed tube;

Reference yield:

tert-butyl 3-bromo-5-methoxy-1H-indole-1-carboxylate (348640-11-9) + bis(pinacol)diborane (73183-34-3) → tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate (1256359-99-5)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dimethyl sulfoxide; at 80 ℃; Inert atmosphere;

upstream raw materials:

5-methoxylindole

3-iodo-5-methoxy-1H-indole

3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester

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

Downstream raw materials:

tert-butyl 5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-1-carboxylate

tert-butyl 3-(5-fluoro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-5-methoxy-1H-indole-1-carboxylate