N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide

Base Information

• Chemical Name: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide
• CAS No.: 885126-35-2
• Molecular Formula: C₂₇H₂₆N₄O₂S
• Molecular Weight: 470.595
• Mol file: 885126-35-2.mol

Synonyms:N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide

Chemical Property of N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide

Chemical Property:

• Boiling Point: 714.2 °C at 760 mmHg
• Flash Point: 385.8 °C
• PSA: 97.83000
• Density: 1.28 g/cm³
• LogP: 6.38640

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Axitinib Tetrahydro-2H-pyran is an intermediate in the synthesis of Axitinib (A794650). The Tetrahydro-2H-pyran moiety acts as a protecting group.

Technology Process of N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide

There total 20 articles about N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide 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: 87.2%

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole + N-methyl-2-sulfanylbenzamide (20054-45-9) → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

N-methyl-2-sulfanylbenzamide; With potassium hydroxide; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Inert atmosphere;

With copper(l) iodide; 1,2-diamino-benzene; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Inert atmosphere;

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole; In N,N-dimethyl-formamide; at 60 - 120 ℃; Temperature; Inert atmosphere;

Reference yield: 70.0%

3,4-dihydro-2H-pyran (110-87-2) + axitinib (319460-85-0,885126-40-9) → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 80 ℃; for 16h;

Reference yield: 62.0%

N-methyl-2-sulfanylbenzamide (20054-45-9) + (E)-6-bromo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In neat (no solvent); for 0.833333h; chemoselective reaction; Milling;

DOI:10.3762/bjoc.14.66

upstream raw materials:

2-vinylpyridine

N-1 THP-protected 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

N-methyl-2-sulfanylbenzamide

(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Refernces

• 1、 Yu, Jingbo,Hong, Zikun,Yang, Xinjie,Jiang, Yu,Jiang, Zhijiang,Su, Weike. "Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib". supporting information. p. 786 - 795. Retrieved 2018/04/16.
• 2、 -. "A process for the preparation of intermediates axi for Nepal the preparation and application of axi for Nepal". Paragraph 0076; 0077; 0078; 0079. . Retrieved 2016/10/07.