4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester
• CAS No.: 1339955-99-5
• Molecular Formula: C₂₄H₂₇ClN₄O₃
• Molecular Weight: 454.956
• Mol file: 1339955-99-5.mol

Synonyms:4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester

Chemical Property of 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester

There total 3 articles about 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester 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: 42.0%

phenylmethyl 1-piperazinecarboxylate (31166-44-6) + 3-bromo-6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1339955-83-7) → 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester (1339955-99-5)

Guidance literature:

With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 6h; Sealed tube; Inert atmosphere; Reflux;

DOI:10.1055/s-0030-1260110

Reference yield:

6-chloro-1H-indazole (698-25-9) → 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester (1339955-99-5)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine / N,N-dimethyl-formamide / 0 - 20 °C

2: toluene-4-sulfonic acid / ethyl acetate / Reflux

3: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 6 h / Sealed tube; Inert atmosphere; Reflux

With bromine; palladium diacetate; caesium carbonate; toluene-4-sulfonic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; 3: Buchwald-Hartwig C-N coupling reaction;

DOI:10.1055/s-0030-1260110

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + 3-bromo-6-chloro-1H-indazole (885521-34-6) → 4-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester (1339955-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / ethyl acetate / Reflux

2: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 6 h / Sealed tube; Inert atmosphere; Reflux

With palladium diacetate; caesium carbonate; toluene-4-sulfonic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethyl acetate; 2: Buchwald-Hartwig C-N coupling reaction;

DOI:10.1055/s-0030-1260110

upstream raw materials:

3,4-dihydro-2H-pyran

3-bromo-6-chloro-1H-indazole

phenylmethyl 1-piperazinecarboxylate

3-bromo-6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Refernces