7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester
• CAS No.: 155206-75-0
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• DSSTox Substance ID: DTXSID401126891
• Nikkaji Number: J2.788.783J
• Mol file: 155206-75-0.mol

Synonyms:DTXSID401126891;1,1-Dimethylethyl 7-(2-formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylate;7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester;155206-75-0

Chemical Property of 7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 383.17327290
• Heavy Atom Count: 28
• Complexity: 560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=C1C(=CC=C2)C3=CC(=C(C=C3C=O)OC)OC

Technology Process of 7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester

There total 5 articles about 7-(2-Formyl-4,5-dimethoxyphenyl)-2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl 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: 65.0%

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) + 7-(tributylstannyl)-2,3-dihydroindole-1-carboxylic acid tert-butyl ester → tert-Butyl 7-(2-formyl-4,5-dimethoxyphenyl)-2,3-dihydroindole-1-carboxylate (155206-75-0)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 70 ℃; for 50h;

DOI:10.3987/COM-94-6777

Reference yield: 41.0%

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) + 1-(tert-butoxycarbonyl)indoline (143262-10-6) → tert-Butyl 7-(2-formyl-4,5-dimethoxyphenyl)-2,3-dihydroindole-1-carboxylate (155206-75-0)

Guidance literature:

1-(tert-butoxycarbonyl)indoline; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;

With zinc(II) chloride; In tetrahydrofuran; at -78 - 60 ℃;

2-bromo-4,5-dimethoxybenzaldehyde; With palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 60 ℃;

DOI:10.1002/adsc.200900499

Reference yield:

7-(2-{[(E)-1-Isopropyl-2-methyl-propylimino]-methyl}-4,5-dimethoxy-phenyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → tert-Butyl 7-(2-formyl-4,5-dimethoxyphenyl)-2,3-dihydroindole-1-carboxylate (155206-75-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 0.5h; Yield given; Heating;

DOI:10.1021/jo00091a049

upstream raw materials:

2-bromo-4,5-dimethoxybenzaldehyde

2-iodo-4,5-dimethoxybenzaldehyde

1-(tert-butoxycarbonyl)indoline

Downstream raw materials:

Vasconine