1-BOC-2-CHLORO-3-FORMYL-INDOLE

Base Information

• Chemical Name: 1-BOC-2-CHLORO-3-FORMYL-INDOLE
• CAS No.: 180922-71-8
• Molecular Formula: C14H14 Cl N O3
• Molecular Weight: 279.723
• Hs Code.: 2933990090
• Mol file: 180922-71-8.mol

Synonyms:1-BOC-2-CHLORO-3-FORMYL-INDOLE

Chemical Property of 1-BOC-2-CHLORO-3-FORMYL-INDOLE

Chemical Property:

• PSA: 48.30000
• LogP: 3.89040

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl2-chloro-3-formyl-1H-indole-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-BOC-2-CHLORO-3-FORMYL-INDOLE

There total 1 articles about 1-BOC-2-CHLORO-3-FORMYL-INDOLE 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-chloroindole-3-carboxaldehyde (5059-30-3) → 1-(tert-butoxycarbonyl)-2-chloroindole-3-carboxaldehyde (180922-71-8)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2014.01.019

Reference yield: 83.0%

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) + 1-(tert-butoxycarbonyl)-2-chloroindole-3-carboxaldehyde (180922-71-8) → 9-(N-tert-butoxycarbonyl)-4-hydroxy-3-methyl-3-nitro-2-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydrogen sulfide monohydrate; In ethanol; at 20 ℃; for 0.5h; diastereoselective reaction; Green chemistry;

DOI:10.1016/j.tetlet.2012.08.125

Reference yield:

1-(tert-butoxycarbonyl)-2-chloroindole-3-carboxaldehyde (180922-71-8) → 5,12-dihydrocycloocta[1,2b;5,6b']diindole-6,13-dicarboxylic acid dimethyl ester (26612-48-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hexamethylsilazane / tetrahydrofuran / 3 h / Cooling with ice

2: lithium chloride / dimethyl sulfoxide; water / 145 °C

3: acetic acid / 3 h / 140 - 150 °C / Dean-Stark

With potassium hexamethylsilazane; acetic acid; lithium chloride; In tetrahydrofuran; water; dimethyl sulfoxide;

upstream raw materials:

di-tert-butyl dicarbonate

2-chloroindole-3-carboxaldehyde

Downstream raw materials:

2-(4-tolylamino)-9-tert-butoxycarbonyl-1,3-thiazino[6,5-b]indol-4-one

C₂₄H₂₃N₃OS

C₃₂H₃₈N₂O₆

Refernces

• 1、 Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng. "A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes". supporting information. p. 3678 - 3686. Retrieved 2021/05/05.
• 2、 Mortimer, Danny,Whiting, Matthew,Harrity, Joseph P.A.,Jones, Simon,Coldham, Iain. "Synthesis of an azabicyclic framework towards (±)-actinophyllic acid". . p. 1255 - 1257. Retrieved 2014/02/14.