tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• CAS No.: 1391926-50-3
• Molecular Formula: C18H25BN2O4
• Molecular Weight: 344.21
• Mol file: 1391926-50-3.mol

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

Chemical Property of tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Chemical Property:

• PSA: 62.58000
• LogP: 3.11870

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-7-Azaindole-4-BoronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

There total 4 articles about tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]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: 86.4%

4-bromopyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (1228014-35-4) + bis(pinacol)diborane (73183-34-3) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1391926-50-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 6h; Inert atmosphere;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 4-bromo-7-azaindole (348640-06-2) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1391926-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dmap / tetrahydrofuran / 0 - 70 °C

2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

With potassium acetate; triethylamine; dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

4-bromo-7-azaindole (348640-06-2) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1391926-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 6 h / 90 °C / Inert atmosphere

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; triethylamine; In 1,4-dioxane; dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

4-bromo-7-azaindole

4-bromopyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

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