3-(2,5-dichloropyrimidin-4-yl)-1H-indole

Base Information

• Chemical Name: 3-(2,5-dichloropyrimidin-4-yl)-1H-indole
• CAS No.: 937366-57-9
• Molecular Formula: C12H7Cl2N3
• Molecular Weight: 264.114
• Hs Code.: 2933990090
• Mol file: 937366-57-9.mol

Synonyms:3-(2,5-dichloropyriMidin-4-yl)-1H-indole;1H-Indole, 3-(2,5-dichloro-4-pyrimidinyl)-

Chemical Property of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole

Chemical Property:

• PSA: 41.57000
• LogP: 3.93170
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-(2,5-Dichloropyrimidin-4-yl)-1H-indole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(2,5-Dichloropyrimidin-4-yl)-1H-indole is used in the preparation 2-(2,4,5-substituted -anilino)pyrimidine derivatives as EGFR modulators useful for the prevention or treatment of a number of different cancers, in particular non-small cell lung cancer.

Technology Process of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole

There total 5 articles about 3-(2,5-dichloropyrimidin-4-yl)-1H-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: 98.0%

indole (120-72-9) + 2,4,5-trichloropyrimidine (5750-76-5) → 3-(2,5-dichloropyrimidine-4-yl)-1H-indole (937366-57-9)

Guidance literature:

2,4,5-trichloropyrimidine; With aluminum (III) chloride; In 1,2-dichloro-ethane; at 80 ℃; for 0.5h; Inert atmosphere;

indole; In 1,2-dichloro-ethane; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c01171

Reference yield: 75.0%

3-(2,5-dichloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole (882562-40-5) → 3-(2,5-dichloropyrimidine-4-yl)-1H-indole (937366-57-9)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 75 ℃; for 3h;

Reference yield:

1-(phenylsulfonyl)-1H-indol-3-ylboronic acid (129271-98-3) → 3-(2,5-dichloropyrimidine-4-yl)-1H-indole (937366-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃ / Pd(PPh₃)4 / acetonitrile; H₂O / 1.5 h / Heating

2: KOH / methanol / 0.5 h / Heating

With potassium hydroxide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; water; acetonitrile; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2007.03.078

upstream raw materials:

2,4,5-trichloropyrimidine

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

3-(2,5-dichloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole

1-(phenylsulfonyl)-1H-indol-3-ylboronic acid

Downstream raw materials:

5-Chloro-4-(1H-indol-3-yl)-N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)pyrimidin-2-amine

AZD3436

Refernces

• 1、 -. "AMINOPYRIMIDINE COMPOUNDS". Paragraph 0198. . Retrieved 2021/07/10.
• 2、 Fuchida, Hirokazu,Hosokawa, Keitaro,Inamori, Ryo,Koyanagi, Satoru,Kuwata, Keiko,Matsunaga, Naoya,Ohdo, Shigehiro,Ojida, Akio,Ono, Mayumi,Sato, Mami,Shibata, Tomohiro,Shindo, Naoya,Tokunaga, Keisuke,Watari, Kosuke,Xiao-Lin, Guo. "Selective Covalent Targeting of Mutated EGFR(T790M) with Chlorofluoroacetamide-Pyrimidines". supporting information. p. 1137 - 1144. Retrieved 2020/07/04.