methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate

Base Information

• Chemical Name: methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate
• CAS No.: 107754-15-4
• Molecular Formula: C19H18 N2 O5
• Molecular Weight: 354.362
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID601162118
• Mol file: 107754-15-4.mol

Synonyms:107754-15-4;methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate;methyl 3-methoxy-4-[(1-methyl-5-nitroindol-3-yl)methyl]benzoate;Methyl 3-methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoate;methyl-benzoate,zafirlukast,;DMPXTRBUJIRVOO-UHFFFAOYSA-N;SCHEMBL3679305;DTXSID601162118;methyl 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)benzoate;methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)-benzoate;3-Methoxy-4-(1-methyl-5-nitro-1H-indol-3-ylmethyl)-benzoic acid methyl ester

Chemical Property of methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate

Chemical Property:

• Melting Point: 149-150 °C
• Boiling Point: 542.5±50.0 °C(Predicted)
• PSA: 86.28000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 3.99570
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 354.12157168
• Heavy Atom Count: 26
• Complexity: 523

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=C1C=CC(=C2)[N+](=O)[O-])CC3=C(C=C(C=C3)C(=O)OC)OC
• Uses: Methyl 3-Methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoate is an intermediate in the synthesis of Methyl 4-[(5-Amino-1-methylindol-3-yl)methyl]-3-methoxybenzoate (M258650), also an intermediate in the preparation of Zafirlukast (Z125000), a potent, selective and orally active cysteinyl leukotriene type 1 receptor antagonist.

Technology Process of methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate

There total 16 articles about methyl 3-methoxy-4-(1-methyl-5-nitro-1H-indol-3-yl)methylbenzoate 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: 94.0%

C25H22N2O7S + methyl iodide (74-88-4) → 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester (107754-15-4)

Guidance literature:

C₂₅H₂₂N₂O₇S; With lithium hydroxide; In methanol; at 60 ℃;

methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50 ℃;

DOI:10.1016/j.tetlet.2020.152123

Reference yield: 89.7%

1-methyl-5-nitro-1H-indole (29906-67-0) + methyl 4-(bromomethyl)-3-methoxybenzoate (70264-94-7) → 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester (107754-15-4)

Guidance literature:

1-methyl-5-nitro-1H-indole; In dichloromethane; at 5 ℃; for 2h;

With diethyl aluminiumcholoride; In dichloromethane; at 40 ℃; for 6h; Inert atmosphere;

methyl 4-(bromomethyl)-3-methoxybenzoate; In dichloromethane; at 35 ℃; for 7h; Temperature;

Reference yield: 80.0%

4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (107786-36-7) + methyl iodide (74-88-4) → 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid methyl ester (107754-15-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

upstream raw materials:

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

methyl iodide

1-methyl-5-nitro-1H-indole

methyl 4-(bromomethyl)-3-methoxybenzoate

Downstream raw materials:

methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate