tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate
• CAS No.: 877399-74-1
• Molecular Formula: C19H32BN3O4
• Molecular Weight: 377.292
• Hs Code.: 2934999090
• Mol file: 877399-74-1.mol

Synonyms:1-[1-(tert-Butoxycarbonyl)piperidin-4-yl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl)piperidine-1-carboxylicacid tert-butyl ester;4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylicacid tert-butyl ester;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate;

Chemical Property of tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Chemical Property:

• Melting Point: 114.0 to 118.0 °C
• Refractive Index: 1.539
• Boiling Point: 492.803 °C at 760 mmHg
• PKA: 2.89±0.19(Predicted)
• Flash Point: 251.838 °C
• PSA: 65.82000
• Density: 1.14 g/cm³
• LogP: 2.69220
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

99% ^*data from raw suppliers

1-(1-Boc-4-piperidyl)pyrazole-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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

There total 20 articles about tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-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: 94.0%

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (877399-50-3) + bis(pinacol)diborane (73183-34-3) → tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-74-1)

Guidance literature:

With C₅₄H₄₄NO₂PPdS; potassium acetate; In tetrahydrofuran; at 80 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02414

Reference yield: 87.9%

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-73-0) + bis(pinacol)diborane (73183-34-3) → tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-74-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 2h; Inert atmosphere;

Reference yield: 81.0%

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-73-0) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-74-1)

Guidance literature:

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate; With isopropylmagnesium chloride; In tetrahydrofuran; at -10 - 0 ℃; for 5.25h; Large scale reaction;

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at 20 - 25 ℃; for 10.75h; Large scale reaction;

DOI:10.1021/op200131n

upstream raw materials:

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

bis(pinacol)diborane

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

tert-butyl 4-(4-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

4-(4-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(4-(1-(5-acetamido-2',4'-difluorobiphenyl-3-yl)-1H-benzo[d]-imidazol-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

N-(3-(5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1H-pyrazol-1-yl)phenyl)acetamide

Refernces

• 1、 -. "DEGRADATION OF BRUTON'S TYROSINE KINASE (BTK) BY CONJUGATION OF BTK INHIBITORS WITH E3 LIGASE LIGAND AND METHODS OF USE". Paragraph 0228-0229. . Retrieved 2021/11/06.
• 2、 -. "Pyrrolo[2, 3-d] pyrimidine derivatives containing piperidine as well as preparation and application thereof". . . Retrieved 2020/09/16.