tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate
• CAS No.: 1174038-67-5
• Molecular Formula: C₁₈H₂₅BN₂O₄
• Molecular Weight: 344.218
• Mol file: 1174038-67-5.mol

Synonyms:tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate;tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate;1-N-Boc-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,3-c]pyridine;tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-c]pyridine-1-carboxylate

Chemical Property of tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Chemical Property:

• Melting Point: 114-124 °C
• Boiling Point: 470.1±48.0 °C(Predicted)
• PKA: 6.20±0.30(Predicted)
• PSA: 62.58000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.11870
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate functions as a reagent used in the preparation of pyrrolo[2,3-c]pyridinylpyrimidinylamines as antitumor agents

Technology Process of tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

There total 5 articles about tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-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: 57.0%

→ tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo [2,3-c]pyridine-1-carboxylate (1174038-67-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

In tetrahydrofuran; at -78 ℃; for 2h;

Reference yield: 14.0%

tert-butyl 1H-pyrrolo [2,3-c]pyridine-1-carboxylate (370880-82-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo [2,3-c]pyridine-1-carboxylate (1174038-67-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 55 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo901822b

Reference yield:

bis(pinacol)diborane (73183-34-3) + tert-butyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo [2,3-c]pyridine-1-carboxylate (1174038-67-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 4h; Inert atmosphere;

upstream raw materials:

tert-butyl 1H-pyrrolo [2,3-c]pyridine-1-carboxylate

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

tert-butyl 3-iodo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

bis(pinacol)diborane

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