ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

Base Information

• Chemical Name: ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate
• CAS No.: 1254036-81-1
• Molecular Formula: C₁₉H₁₄ClN₃O₅S
• Molecular Weight: 431.856
• Mol file: 1254036-81-1.mol

Synonyms:ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

Chemical Property of ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

There total 13 articles about ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate 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: 97.0%

ethyl 2-chloro-1,3-oxazole-5-carboxylate (862599-47-1) + 6-chloro-1-(phenylsulfonyl)-4-(trimethylstannanyl)-1H-indazole (1254036-80-0) → ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1254036-81-1)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00767

Reference yield:

5-chloro-2-methyl-1,3-dinitro-benzene (35572-79-3) → ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1254036-81-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diammonium sulfide / water; ethanol

2.1: sodium nitrite

3.1: nickel; hydrazine hydrate

4.1: acetic acid; acetic anhydride

5.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / tetrahydrofuran

6.1: lithium hexamethyldisilazane; zinc(II) chloride / tetrahydrofuran / -10 °C

6.2: 60 °C

With diammonium sulfide; tetra(n-butyl)ammonium hydrogensulfate; acetic anhydride; nickel; hydrazine hydrate; acetic acid; sodium hydroxide; zinc(II) chloride; lithium hexamethyldisilazane; sodium nitrite; In tetrahydrofuran; ethanol; water;

DOI:10.1021/acs.oprd.0c00486

Reference yield:

6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole (1254036-94-6) + oxazol-5-yl-carboxylic acid ethyl ester (118994-89-1) → ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1254036-81-1)

Guidance literature:

oxazol-5-yl-carboxylic acid ethyl ester; With zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; at -15 - -5 ℃; for 1.25h; Inert atmosphere;

6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 57 - 63 ℃; for 6h; Inert atmosphere;

upstream raw materials:

ethyl 2-chloro-1,3-oxazole-5-carboxylate

6-chloro-1-(phenylsulfonyl)-4-(trimethylstannanyl)-1H-indazole

benzenesulfonyl chloride

6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole

Downstream raw materials:

ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

{2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazol-5-yl}methanol

{2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazol-5-yl}methanol

4-[5-(bromomethyl)-1,3-oxazol-2-yl]-6-chloro-1-(phenylsulfonyl)-1H-indazole