3-Pyridinecarboxamide, N-[2-(dimethylamino)ethyl]-4-[1-[5-methoxy-1-(phenylsulfonyl)-1H-indol- 2-yl]ethyl]-

Base Information

• Chemical Name: 3-Pyridinecarboxamide, N-[2-(dimethylamino)ethyl]-4-[1-[5-methoxy-1-(phenylsulfonyl)-1H-indol- 2-yl]ethyl]-
• CAS No.: 139260-72-3
• Molecular Formula: C27H30N4O4S
• Molecular Weight: 506.626
• Mol file: 139260-72-3.mol

Synonyms:

Chemical Property of 3-Pyridinecarboxamide, N-[2-(dimethylamino)ethyl]-4-[1-[5-methoxy-1-(phenylsulfonyl)-1H-indol- 2-yl]ethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyridinecarboxamide, N-[2-(dimethylamino)ethyl]-4-[1-[5-methoxy-1-(phenylsulfonyl)-1H-indol- 2-yl]ethyl]-

There total 12 articles about 3-Pyridinecarboxamide, N-[2-(dimethylamino)ethyl]-4-[1-[5-methoxy-1-(phenylsulfonyl)-1H-indol- 2-yl]ethyl]- 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:

cinchomeronic anhydride (4664-08-8) → 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(2-dimethylamino-ethyl)-nicotinamide (139260-72-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / CH₂Cl₂ / 18 h / Ambient temperature

2: SOCl₂ / 1.5 h / Heating

3: CH₂Cl₂ / 18 h / Ambient temperature

4: 49.5 percent / diethyl ether / 18 h / Ambient temperature

5: 1) BuLi / 1) THF, room temp., 2 h; 2) THF, -13 deg C, then 18 h at room temp.

6: 80 percent / aq. HCl / 18 h

7: 62 percent / activated Zn, aq. HCOOH / 12 h / Heating

8: N,N'-carbonyldiimidazole / dimethylformamide / Ambient temperature

With hydrogenchloride; n-butyllithium; formic acid; thionyl chloride; 1,1'-carbonyldiimidazole; zinc; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/P19910003165

Reference yield:

nicotinic acid (59-67-6) → 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(2-dimethylamino-ethyl)-nicotinamide (139260-72-3)

Guidance literature:

Multi-step reaction with 7 steps

1: SOCl₂ / 18 h / Ambient temperature

2: CH₂Cl₂ / 18 h / Ambient temperature

3: 1) lithium diisopropylamide / 1) Et₂O, -70 deg C, 2 h; 2) Et₂O, -50 deg C, then 18 h at room temp.

4: 1) BuLi / 1) THF, room temp., 2 h; 2) THF, -13 deg C, then 18 h at room temp.

5: 80 percent / aq. HCl / 18 h

6: 62 percent / activated Zn, aq. HCOOH / 12 h / Heating

7: N,N'-carbonyldiimidazole / dimethylformamide / Ambient temperature

With hydrogenchloride; n-butyllithium; formic acid; thionyl chloride; 1,1'-carbonyldiimidazole; zinc; lithium diisopropyl amide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/P19910003165

Reference yield:

3-pyridinecarbonyl chloride (10400-19-8) → 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(2-dimethylamino-ethyl)-nicotinamide (139260-72-3)

Guidance literature:

Multi-step reaction with 6 steps

1: CH₂Cl₂ / 18 h / Ambient temperature

2: 1) lithium diisopropylamide / 1) Et₂O, -70 deg C, 2 h; 2) Et₂O, -50 deg C, then 18 h at room temp.

3: 1) BuLi / 1) THF, room temp., 2 h; 2) THF, -13 deg C, then 18 h at room temp.

4: 80 percent / aq. HCl / 18 h

5: 62 percent / activated Zn, aq. HCOOH / 12 h / Heating

6: N,N'-carbonyldiimidazole / dimethylformamide / Ambient temperature

With hydrogenchloride; n-butyllithium; formic acid; 1,1'-carbonyldiimidazole; zinc; lithium diisopropyl amide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/P19910003165

upstream raw materials:

4-<1-(5-Methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinic Acid

N,N-dimethylethylenediamine

nicotinic acid

3-pyridinecarbonyl chloride