(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

Base Information

• Chemical Name: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile
• CAS No.: 1146629-84-6
• Molecular Formula: C17H26BN3O2
• Molecular Weight: 315.223
• Hs Code.: 2934999090
• Mol file: 1146629-84-6.mol

Synonyms:(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile;1H-Pyrazole-1-propanenitrile, b-cyclopentyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, (bR)-;(R)-3-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitri;(betaR)-beta-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile

Chemical Property of (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

Chemical Property:

• Boiling Point: 471.8±25.0 °C(Predicted)
• PKA: 1.71±0.10(Predicted)
• PSA: 60.07000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 2.82728
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

(R)-3-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

There total 12 articles about (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 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: 43.0%

(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanecarbonitrile (1146629-83-5) + bis(pinacol)diborane (73183-34-3) → (3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (1146629-84-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; at 120 ℃; for 2h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.jmedchem.0c01952

Reference yield:

3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile + bis(pinacol)diborane (73183-34-3) → (3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (1146629-84-6)

Guidance literature:

With potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 120 ℃; for 1h; microwave irraddiation;

Reference yield:

racemic-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (1153949-38-2) → (3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (1146629-84-6) + (S)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (1236033-24-1)

Guidance literature:

With Chiralpak IA; In hexanes; ethanol; at 20 ℃; Purification / work up;

upstream raw materials:

(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanecarbonitrile

bis(pinacol)diborane

racemic-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

(3R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanal

Downstream raw materials:

ruxolitinib

Refernces

• 1、 Haydl, Alexander M.,Xu, Kun,Breit, Bernhard. "Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes". supporting information. p. 7149 - 7153. Retrieved 2015/06/08.
• 2、 Lin, Qiyan,Meloni, David,Pan, Yongchun,Xia, Michael,Rodgers, James,Shepard, Stacey,Li, Mei,Galya, Laurine,Metcalf, Brian,Yue, Tai-N,Liu, Pingli,Zhou, Jiacheng. "Enantioselective synthesis of janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction". supporting information; experimental part. p. 1999 - 2002. Retrieved 2009/09/06.