tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin -2-yl]carbamate

Base Information

• Chemical Name: tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin -2-yl]carbamate
• CAS No.: 1095708-32-9
• Molecular Formula: C16H25BN2O4
• Molecular Weight: 320.196
• Hs Code.: 2934999090
• Mol file: 1095708-32-9.mol

Synonyms:tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylcarbamate;Boc-2-Aminopyridine-4-boronic acid pinacol ester;2-(Boc-amino)pyridine-4-boronic acid pinacol ester;2-(tert-Butoxycarbonylamino)pyridine-4-boronic acid pinacol ester;tert-butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrid-2-yl]carbamate;

Chemical Property of tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin -2-yl]carbamate

Chemical Property:

• Boiling Point: 400.7±30.0 °C(Predicted)
• PKA: 12.66±0.70(Predicted)
• PSA: 69.68000
• Density: 1.10
• LogP: 2.80080
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

Boc-2-aminopyridine-4-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin -2-yl]carbamate

There total 5 articles about tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin -2-yl]carbamate 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: 98.0%

4-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine (1195995-72-2) + di-tert-butyl dicarbonate (24424-99-5) → N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]carbamic acid 1,1-dimethylethyl ester (1095708-32-9)

Guidance literature:

In tert-butyl alcohol; at 35 ℃; for 18h; Inert atmosphere;

Reference yield: 78.0%

(4-bromopyridin-2-yl)-carbamic acid tert-butyl ester (207799-10-8) + bis(pinacol)diborane (73183-34-3) → N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]carbamic acid 1,1-dimethylethyl ester (1095708-32-9)

Guidance literature:

With (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-N-methylamino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium acetate; In 1,4-dioxane; at 80 ℃; for 2h;

DOI:10.1021/acs.jmedchem.7b00316

Reference yield:

2-amino-4-bromopyridine (84249-14-9) → N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]carbamic acid 1,1-dimethylethyl ester (1095708-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.17 h / -5 °C

1.2: 1 h / 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl-formamide / 5 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

upstream raw materials:

(4-bromopyridin-2-yl)-carbamic acid tert-butyl ester

bis(pinacol)diborane

2-amino-4-bromopyridine

di-tert-butyl dicarbonate

Downstream raw materials:

{4-[6-(5-benzylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-methylimidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl}amine

{4-[6-(5-benzylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-2-methylimidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl}methylamine

C₂₈H₂₇F₂N₅O₃

5-[5-(2-amino-pyridin-4-yl)-2-methyl-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide