3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide

Base Information

• Chemical Name: 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide
• CAS No.: 545432-32-4
• Molecular Formula: C₂₀H₂₀F₃N₃O₂
• Molecular Weight: 391.393
• Mol file: 545432-32-4.mol

Synonyms:3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide

Chemical Property of 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide

There total 3 articles about 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide 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: 61.0%

3-Trifluoromethylbenzaldehyde (454-89-7) + 2-(N,N-dimethylhydrazinecarbonyl)-1-methylindole (545432-27-7) → 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide (545432-32-4)

Guidance literature:

2-(N,N-dimethylhydrazinecarbonyl)-1-methylindole; With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

3-Trifluoromethylbenzaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 8h;

DOI:10.1055/s-2003-36786

Reference yield:

1-methyl-1H-indole-2-carbonyl chloride (118618-61-4) → 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide (545432-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CH₂Cl₂ / 20 °C

2.1: TMEDA; t-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

2.2: 61 percent / tetrahydrofuran; hexane / 8 h / -78 - 20 °C

With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-2003-36786

Reference yield:

N-methyl-1H-indole-2-carboxylic acid (16136-58-6) → 3-[hydroxy-(3-trifluoromethyl-phenyl)-methyl]-1-methyl-1H-indole-2-carboxylic acid N',N'-dimethyl-hydrazide (545432-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: SOCl₂ / toluene

2.1: CH₂Cl₂ / 20 °C

3.1: TMEDA; t-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

3.2: 61 percent / tetrahydrofuran; hexane / 8 h / -78 - 20 °C

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1055/s-2003-36786

upstream raw materials:

3-Trifluoromethylbenzaldehyde

2-(N,N-dimethylhydrazinecarbonyl)-1-methylindole

1-methyl-1H-indole-2-carbonyl chloride

N-methyl-1H-indole-2-carboxylic acid