(E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide

Base Information

• Chemical Name: (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide
• CAS No.: 1421849-47-9
• Molecular Formula: C₁₇H₂₁N₃O₂
• Molecular Weight: 299.373
• Mol file: 1421849-47-9.mol

Synonyms:(E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide

Chemical Property of (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide

There total 4 articles about (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide 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: 16.4%

(E)-2-(4-methoxyphenyl)vinylboronic acid (72316-18-8) + 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxamide (1421849-18-4) → (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide (1421849-47-9)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 40 ℃; for 14h; Inert atmosphere;

Reference yield:

5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylic acid (98534-79-3) → (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide (1421849-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride; benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; water / 14 h / 20 °C

2: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

Reference yield:

ethyl 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylate (1245272-40-5) → (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide (1421849-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide; water / ethanol; tetrahydrofuran / 2.5 h / 60 °C

2: ammonium chloride; benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; water / 14 h / 20 °C

3: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; water; palladium diacetate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

1-(tert-butyl)-5-amino-pyrazole-4-carboxylic acid ethyl ester

ethyl 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylate

5-bromo-1-tert-butyl-1H-pyrazole-4-carboxylic acid

(E)-2-(4-methoxyphenyl)vinylboronic acid

Refernces