N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide

Base Information

• Chemical Name: N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide
• CAS No.: 436091-30-4
• Molecular Formula: C₂₃H₂₄N₄O₄S
• Molecular Weight: 452.534
• Mol file: 436091-30-4.mol

Synonyms:

Chemical Property of N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide

There total 13 articles about N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide 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: 32.0%

acetylguanidine (5699-40-1) + 1-bromo-3-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-butan-2-one (436097-25-5) → N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide (436091-30-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 96h;

DOI:10.1016/S0040-4039(01)02331-0

Reference yield:

3-methyl-2-nitrophenol (4920-77-8) → N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide (436091-30-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / Br₂ / acetic acid / 6 h

2: 100 percent / K₂CO₃ / Heating

3: pyrrolidine / dimethylformamide / 14 h / 110 °C

4: NH₂NH₂*H₂O; Raney-Ni / methanol; tetrahydrofuran

5: 82 percent / nBuLi / tetrahydrofuran

6: 92 percent / nBuLi; BF₃*Et₂O; CuCN / tetrahydrofuran / -78 °C

7: 98 percent / nBu₄NF

8: 89 percent / NaH

9: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -40 - 20 °C

10: 96 percent / Et₃N

11: 88 percent / LiBr / acetone

12: 32 percent / dimethylformamide / 96 h / 20 °C

With pyrrolidine; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; bromine; nickel; sodium hydride; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; 3: Batcho-Leimgruber indole synthesis / 9: Swern-oxidation;

DOI:10.1016/S0040-4039(01)02331-0

Reference yield:

4-bromo-3-methyl-2-nitro-phenol (85598-12-5) → N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide (436091-30-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / K₂CO₃ / Heating

2: pyrrolidine / dimethylformamide / 14 h / 110 °C

3: NH₂NH₂*H₂O; Raney-Ni / methanol; tetrahydrofuran

4: 82 percent / nBuLi / tetrahydrofuran

5: 92 percent / nBuLi; BF₃*Et₂O; CuCN / tetrahydrofuran / -78 °C

6: 98 percent / nBu₄NF

7: 89 percent / NaH

8: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -40 - 20 °C

9: 96 percent / Et₃N

10: 88 percent / LiBr / acetone

11: 32 percent / dimethylformamide / 96 h / 20 °C

With pyrrolidine; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; nickel; sodium hydride; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Batcho-Leimgruber indole synthesis / 8: Swern-oxidation;

DOI:10.1016/S0040-4039(01)02331-0

upstream raw materials:

acetylguanidine

1-bromo-3-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-butan-2-one

3-methyl-2-nitrophenol

4-bromo-3-methyl-2-nitro-phenol