4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Base Information

• Chemical Name: 4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• CAS No.: 406170-08-9
• Molecular Formula: C₁₃H₁₃ClINO₂
• Molecular Weight: 377.609
• Mol file: 406170-08-9.mol

Synonyms:4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-Chloro-3-iodoindole, N-BOC protected

Chemical Property of 4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property:

• Boiling Point: 417.14 °C at 760 mmHg
• Flash Point: 206.079 °C
• PSA: 31.23000
• Density: 1.648 g/cm³
• LogP: 4.68250

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl4-chloro-3-iodo-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 4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

There total 4 articles about 4-CHLORO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL 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:

4-chloro-3-dimethylaminomethylindole (40247-57-2) → tert-butyl 4-chloro-3-iodo-1H-indolecarboxylate (406170-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NIS / CH₂Cl₂ / 0.17 h

2: 80 mg / TEA / DMAP / CH₂Cl₂ / 0.25 h

With N-iodo-succinimide; TEA; dmap; In dichloromethane; 1: retro-Mannich fragmentation;

DOI:10.1021/ol017310m

Reference yield:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → tert-butyl 4-chloro-3-iodo-1H-indolecarboxylate (406170-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: t-BuLi / diethyl ether; pentane / 1 h / 0 °C

1.2: 64 percent / Cl₃CCCl₃ / tetrahydrofuran; diethyl ether; pentane / 5 h / -78 - 20 °C

2.1: TBAF / tetrahydrofuran / 0.17 h / 20 °C

3.1: NIS / CH₂Cl₂ / 0.17 h

4.1: 80 mg / TEA / DMAP / CH₂Cl₂ / 0.25 h

With N-iodo-succinimide; TEA; tetrabutyl ammonium fluoride; tert.-butyl lithium; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 3.1: retro-Mannich fragmentation;

DOI:10.1021/ol017310m

Reference yield:

N-{[4-chloro-1-(1,1,1-triisopropylsilyl)-1H-3-indolyl]methyl}-N,N-dimethylamine (146886-60-4) → tert-butyl 4-chloro-3-iodo-1H-indolecarboxylate (406170-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 0.17 h / 20 °C

2: NIS / CH₂Cl₂ / 0.17 h

3: 80 mg / TEA / DMAP / CH₂Cl₂ / 0.25 h

With N-iodo-succinimide; TEA; tetrabutyl ammonium fluoride; dmap; In tetrahydrofuran; dichloromethane; 2: retro-Mannich fragmentation;

DOI:10.1021/ol017310m

upstream raw materials:

di-tert-butyl dicarbonate

4-chloro-3-dimethylaminomethylindole

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

N-{[4-chloro-1-(1,1,1-triisopropylsilyl)-1H-3-indolyl]methyl}-N,N-dimethylamine

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