[5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester

Base Information

• Chemical Name: [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester
• CAS No.: 1275597-97-1
• Molecular Formula: C₂₉H₂₆ClN₃O₅
• Molecular Weight: 531.996
• Mol file: 1275597-97-1.mol

Synonyms:[5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester

Chemical Property of [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester

There total 5 articles about [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl 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: 59.0%

{5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1H-indol-3-yl}acetic acid methyl ester (1275597-91-5) + 4-chloro-benzoyl chloride (122-01-0) → [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester (1275597-97-1)

Guidance literature:

{5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1H-indol-3-yl}acetic acid methyl ester; With dmap; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h; Inert atmosphere;

4-chloro-benzoyl chloride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.03.027

Reference yield:

5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9) → [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester (1275597-97-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 0 - 20 °C / Inert atmosphere

2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran; toluene / 3 h / 20 °C

3.1: dmap; sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With dmap; thionyl chloride; tributylphosphine; sodium hydride; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.03.027

Reference yield:

(5-hydroxy-1H-indol-3-yl)acetic acid methyl ester (15478-18-9) → [5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid methyl ester (1275597-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran; toluene / 3 h / 20 °C

2.1: dmap; sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With dmap; tributylphosphine; sodium hydride; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; mineral oil; 1.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.03.027

upstream raw materials:

2-chloro-1,3-benzoxazole

{5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1H-indol-3-yl}acetic acid methyl ester

4-chloro-benzoyl chloride

(5-hydroxy-1H-indol-3-yl)acetic acid methyl ester