1-Boc-4-ethynyl-1H-pyrazole

Base Information

• Chemical Name: 1-Boc-4-ethynyl-1H-pyrazole
• CAS No.: 1093193-29-3
• Molecular Formula: C10H12N2O2
• Molecular Weight: 192.217
• Hs Code.: 2933199090
• Mol file: 1093193-29-3.mol

Synonyms:1-Boc-4-ethynyl-1H-pyrazole;tert-butyl 4-ethynyl-1H-pyrazole-1-carboxylate;1H-Pyrazole-1-carboxylic acid, 4-ethynyl-, 1,1-dimethylethyl ester

Chemical Property of 1-Boc-4-ethynyl-1H-pyrazole

Chemical Property:

• Boiling Point: 278.9±32.0 °C(Predicted)
• PKA: -2.70±0.12(Predicted)
• PSA: 44.12000
• Density: 1.03±0.1 g/cm3(Predicted)
• LogP: 1.64760

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-4-ethynyl-1H-pyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Boc-4-ethynyl-1H-pyrazole

There total 3 articles about 1-Boc-4-ethynyl-1H-pyrazole 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: 82.0%

tert-butyl 4-((trimethylsilyl)ethynyl)-1H-pyrazole-1-carboxylate (1093193-28-2) → 4-ethynyl-1H-pyrazole-1-carboxylate tert-butyl ester (1093193-29-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 5 ℃; for 0.333333h;

Reference yield:

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester (121669-70-3) → 4-ethynyl-1H-pyrazole-1-carboxylate tert-butyl ester (1093193-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; bis(triphenylphosphine)palladium(II) dichloride; triethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With copper(l) iodide; bis(triphenylphosphine)palladium(II) dichloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1: Sonogashira coupling;

DOI:10.1039/c1ob05586k

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 4-ethynyl-1H-pyrazole-1-carboxylate tert-butyl ester (1093193-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 3 h / 20 °C

2: palladium diacetate; triphenylphosphine; diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 1.25 h / 60 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 5 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; palladium diacetate; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm401395s

upstream raw materials:

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester

tert-butyl 4-((trimethylsilyl)ethynyl)-1H-pyrazole-1-carboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

1-benzyl-4-(1H-pyrazol-4-yl)-1H-1,2,3-triazole

C₁₇H₁₉N₅O₂

tert-butyl 4-(6-(4-fluorophenylamino)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

N-(4-fluorophenyl)-1-(methylsulfonyl)-2-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridin-6-amine