Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Base Information

• Chemical Name: Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate
• CAS No.: 107754-14-3
• Molecular Formula: C19H20 N2 O3
• Molecular Weight: 324.379
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50458890
• Wikidata: Q82282444
• Mol file: 107754-14-3.mol

Synonyms:107754-14-3;Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate;methyl 4-[(5-amino-1-methylindol-3-yl)methyl]-3-methoxybenzoate;4-(5-AMINO-1-METHYL-1H-INDOL-3-YLMETHYL)-3-METHOXY-BENZOIC ACID METHYL ESTER;Benzoic acid,4-[(5-amino-1-methyl-1H-indol-3-yl)methyl]-3-methoxy-, methyl ester;Methyl 4-[(5-amino-1-methyl-1H-indol-3-yl)methyl]-3-methoxybenzoate;SCHEMBL3674759;DTXSID50458890;WEMIOTLFXSHMSS-UHFFFAOYSA-N;AKOS015898447;AC-33641;methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate;methyl 3-methoxy-4-(1-methyl-5-amino-1H-indol-3-yl)methylbenzoate;methyl 4-(5-amino-1-methylindol -3-ylmethyl)-3-methoxybenzoate;methyl 4-(5-amino-1-methylindol-3- ylmethyl)-3-methoxybenzoate;Benzoic acid,4-[(5-amino-1-methyl-1H-indol-3-yl)methyl]-3-methoxy-,methyl ester

Chemical Property of Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Chemical Property:

• PSA: 66.48000
• LogP: 3.72770
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.14739250
• Heavy Atom Count: 24
• Complexity: 444

Purity/Quality:

99%, ^*data from raw suppliers

Methyl4-[(5-Amino-1-methylindol-3-yl)methyl]-3-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=C1C=CC(=C2)N)CC3=C(C=C(C=C3)C(=O)OC)OC
• Uses: Methyl 4-[(5-Amino-1-methylindol-3-yl)methyl]-3-methoxybenzoate is an intermediate used in the preparation of Zafirlukast (Z125000), a potent, selective and orally active cysteinyl leukotriene type 1 receptor antagonist.

Technology Process of Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

There total 11 articles about Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate 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%

3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester (107754-15-4) → methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate (107754-14-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 2h; under 2587.7 Torr;

DOI:10.1021/jm00168a037

Reference yield: 44.0%

1-methyl-5-nitro-1H-indole (29906-67-0) + methyl 4-(bromomethyl)-3-methoxybenzoate (70264-94-7) → C28H28N4O3 + C29H30N2O6 + methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate (107754-14-3)

Guidance literature:

1-methyl-5-nitro-1H-indole; methyl 4-(bromomethyl)-3-methoxybenzoate; With copper(I) oxide; In 1,4-dioxane; at 95 - 100 ℃; Large scale reaction;

With hydrogen; In water; ethyl acetate; at 25 - 30 ℃; under 3677.86 - 4413.43 Torr; Large scale reaction;

DOI:10.1021/op800137b

Reference yield:

methyl 4-methyl-3-methoxybenzoate (3556-83-0) → methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate (107754-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / Reflux; Inert atmosphere

2: iron(III) chloride / 1,4-dioxane / 12 h / 20 °C / Inert atmosphere

3: hydrogen; palladium on activated charcoal / 12 h / 20 °C / Inert atmosphere

With iron(III) chloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; hydrogen; In 1,4-dioxane; chloroform; 2: |Friedel-Crafts Alkylation;

DOI:10.1021/acs.jmedchem.8b00458

upstream raw materials:

3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester

methyl 4-(bromomethyl)-3-methoxybenzoate

4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester

5-nitroindole

Downstream raw materials:

methyl 4-<<5-(N'-cyclopentylureido)-1-methylindol-3-yl>methyl>-3-methoxybenzoate

methyl-4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate