1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester

Base Information

• Chemical Name: 1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester
• CAS No.: 153827-71-5
• Molecular Formula: C17H14INO4S
• Molecular Weight: 455.273
• DSSTox Substance ID: DTXSID80441937
• Nikkaji Number: J754.039F
• Wikidata: Q82258948
• Mol file: 153827-71-5.mol

Synonyms:153827-71-5;1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester;DTXSID80441937;Ethyl 3-iodo-1-(phenylsulfonyl)-1H-indole-2-carboxylate;1-(Phenylsulfonyl)-3-iodo-1H-indole-2-carboxylic acid ethyl ester

Chemical Property of 1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 454.96883
• Heavy Atom Count: 24
• Complexity: 555

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=CC=CC=C2N1S(=O)(=O)C3=CC=CC=C3)I

Technology Process of 1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester

There total 2 articles about 1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl 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: 85.0%

ethyl 3-iodo-1H-indole-2-carboxylate (117637-79-3) + benzenesulfonyl chloride (98-09-9) → ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate (153827-71-5)

Guidance literature:

ethyl 3-iodo-1H-indole-2-carboxylate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.75h; Inert atmosphere;

benzenesulfonyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/ejoc.200800643

Reference yield: 57.0%

C8H8O5 (97037-63-3) + 3-iodo-1-phenylsulfonyl-1H-indole (80360-14-1) → ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate (153827-71-5) + (1-benzenesulfonyl-3-iodo-1H-indol-2-yl)-furan-2-yl-methanone (403642-46-6)

Guidance literature:

3-iodo-1-phenylsulfonyl-1H-indole; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -60 ℃; for 0.166667h;

C₈H₈O₅; In tetrahydrofuran; n-heptane; ethylbenzene; at -60 - 20 ℃; for 1h;

DOI:10.1055/s-2001-18715

Reference yield: 84.0%

ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate (153827-71-5) + phenylboronic acid (98-80-6) → ethyl 3-phenyl-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; cesium fluoride; In 1,4-dioxane; at 90 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2015.12.019

upstream raw materials:

ethyl 3-iodo-1H-indole-2-carboxylate

benzenesulfonyl chloride

C₈H₈O₅

3-iodo-1-phenylsulfonyl-1H-indole

Downstream raw materials:

ethyl 3-(2-formylphenyl)-1-phenylsulfonyl-1H-indole-2-carboxylate

(R,S)-ethyl 1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)ethyl]phenyl}-1H-indole-2-carboxylate

ethyl (R)-1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)ethyl]phenyl}-1H-indole-2-carboxylate

ethyl (S)-1-(benzenesulfonyl)-3-{2-[1-(tert-butyloxycarbonylamino)ethyl]phenyl}-1H-indole-2-carboxylate