1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro-

Base Information

• Chemical Name: 1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro-
• CAS No.: 872675-11-1
• Molecular Formula: C22H18N2O2
• Molecular Weight: 342.397
• DSSTox Substance ID: DTXSID40470440
• Wikidata: Q82298533
• Mol file: 872675-11-1.mol

Synonyms:1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro-;872675-11-1;DTXSID40470440

Chemical Property of 1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro-

Chemical Property:

• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 342.136827821
• Heavy Atom Count: 26
• Complexity: 461

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(N1C(C3=CC=CC=C3)C4=CC=CC=C4)C=CC(=C2)[N+](=O)[O-]

Technology Process of 1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro-

There total 1 articles about 1H-Indole, 1-(diphenylmethyl)-2-methyl-5-nitro- 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: 23.0%

5-nitro-2-methylindole (7570-47-0) + Bromodiphenylmethane (776-74-9) → 1-(diphenylmethyl)-2-methyl-5-nitro-1H-indole (872675-11-1)

Guidance literature:

5-nitro-2-methylindole; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

Bromodiphenylmethane; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jm0507882

Reference yield: 32.0%

1-(diphenylmethyl)-2-methyl-5-nitro-1H-indole (872675-11-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl [1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]oxoacetate (872675-12-2)

Guidance literature:

In diethyl ether; for 0.5h; cooling;

DOI:10.1021/jm0507882

Reference yield:

1-(diphenylmethyl)-2-methyl-5-nitro-1H-indole (872675-11-1) → methyl 4-[2-[5-amino-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethoxy]benzoate (872675-16-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 32 percent / diethyl ether / 0.5 h / cooling

2: 50 percent / BH₃*Me₂S / tetrahydrofuran / 20 h / Heating

3: 63 percent / PPh₃; diisopropyl azodicarboxylate / CH₂Cl₂ / 16 h

4: 48 percent / H₂ / Pd/C / 760 Torr

With di-isopropyl azodicarboxylate; dimethylsulfide borane complex; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Mitsunobu reaction;

DOI:10.1021/jm0507882

upstream raw materials:

5-nitro-2-methylindole

Bromodiphenylmethane

Downstream raw materials:

ethyl [1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]oxoacetate

2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethanol

methyl 4-[2-[5-amino-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethoxy]benzoate

methyl 4-[2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethoxy]benzoate

Refernces