2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate

Base Information

• Chemical Name: 2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate
• CAS No.: 1201657-32-0
• Molecular Formula: C₁₅H₂₅BN₂O₄
• Molecular Weight: 308.185
• Mol file: 1201657-32-0.mol

Synonyms:

Chemical Property of 2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate

Chemical Property:

• Boiling Point: 406.2±25.0 °C(Predicted)
• PKA: 1.53±0.10(Predicted)
• Density: 1.08±0.1 g/cm3(Predicted)

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl2-Methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl 2-Methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate is used as a reactant in the preparation of inhibitors that overcome the G1202R anaplastic lymphoma kinase resistance mutation.

Technology Process of 2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate

There total 7 articles about 2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate 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: 66.0%

ethyl 2-bromoisobutyrate (600-00-0) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → ethyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate (1201657-32-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 10h;

Reference yield: 42.5%

ethyl 2-(4-bromo-1H-pyrazol-1-yl)-2-methylpropanoate (1040377-17-0) + bis(pinacol)diborane (73183-34-3) → ethyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate (1201657-32-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 ℃; for 12h;

Reference yield:

2-(4-iodo-pyrazol-1-yl)-2-methyl-propionic acid ethyl ester (1022151-49-0) + bis(pinacol)diborane (73183-34-3) → ethyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate (1201657-32-0)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl acetamide; at 130 ℃; for 0.5h; Microwave irradiation;

upstream raw materials:

2-(4-iodo-pyrazol-1-yl)-2-methyl-propionic acid ethyl ester

bis(pinacol)diborane

ethyl 2-bromoisobutyrate

pyrazole-4-boronic acid pinacol ester

Downstream raw materials:

N-(2-diethylamino-ethyl)-2-[4-(3-{3-[3-(2,2,2-trifluoro-ethyl)-ureido]-phenyl}-imidazo[1,2-a]pyridin-7-yl)-pyrazol-1-yl]-isobutyramide

2-methyl-2-[4-(3-{3-[3-(2,2,2-trifluoroethyl)ureido]phenyl}imidazo[1,2-a]pyridin-7-yl)pyrazol-1-yl]propionic acid

1-(3-{7-[1-(2-hydroxy-1,1-dimethylethyl)-1H-pyrazol-4-yl]-imidazo[1,2-a]pyridin-3-yl}phenyl)-3-(2,2,2-trifluoroethyl)urea

2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-yl)propan-1-ol

Refernces

• 1、 -. "Fused tricyclic compounds and application thereof in medicaments". Paragraph 0358-0362. . Retrieved 2020/03/17.
• 2、 St-Jean, Frédéric,Remarchuk, Travis,Angelaud, Rémy,Carrera, Diane E.,Beaudry, Danial,Malhotra, Sushant,McClory, Andrew,Kumar, Archana,Ohlenbusch, Gerd,Schuster, Andreas M.,Gosselin, Francis. "Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 2: Development of a Highly Efficient and Regioselective Late-Stage Process". . p. 783 - 793. Retrieved 2019/04/01.