tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate
• CAS No.: 1631145-18-0
• Molecular Formula: C₂₂H₁₉NO₃
• Molecular Weight: 345.398
• Mol file: 1631145-18-0.mol

Synonyms:tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate

Chemical Property of tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate

There total 9 articles about tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate 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: 77.0%

tert-butyl 2-formyl-3-iodo-1H-indole-1-carboxylate (1239321-11-9) + phenylacetylene (536-74-3) → tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate (1631145-18-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 50 ℃; for 6h;

DOI:10.1002/chem.201802350

Reference yield: 72.0%

tert-butyl N-[2-(3-phenylprop-2-ynoyl)phenyl]carbamate + 1-ethoxyacetylene (927-80-0) → tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate (1631145-18-0)

Guidance literature:

1-ethoxyacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 4h;

tert-butyl N-[2-(3-phenylprop-2-ynoyl)phenyl]carbamate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; hexane; water; at 0 - 20 ℃; for 0.5h;

DOI:10.1002/adsc.201301002

Reference yield:

tert-butyl (2-formylphenyl)carbamate (74965-38-1) → tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate (1631145-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 1.33 h / -78 - 20 °C

1.2: 1 h / -78 - -40 °C

2.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 - 0 °C

3.2: 3 h / -78 - 20 °C

3.3: 0.5 h / 0 - 20 °C

With manganese(IV) oxide; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/adsc.201301002

upstream raw materials:

1-ethoxyacetylene

tert-butyl (2-formylphenyl)carbamate

phenylacetylene

tert-butyl [2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenyl]carbamate

Downstream raw materials:

tert-butyl 3-phenyl-9H-pyrido[3,4-b]indole-9-carboxylate

5-methyl-5,11-dihydroindolo[3,2-b]carbazol-6-yl(phenyl)methanone

tert-butyl 12-benzoyl-11-methylindolo[3,2-b]carbazole-5(11H)-carboxylate