methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

Base Information

• Chemical Name: methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
• CAS No.: 1109230-57-0
• Molecular Formula: C₂₅H₂₈N₂O₃
• Molecular Weight: 404.509
• Mol file: 1109230-57-0.mol

Synonyms:methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

Chemical Property of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

There total 8 articles about methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-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:

methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1109230-52-5) + (3‐cyanophenyl)boronic acid (150255-96-2) → methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1109230-57-0)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 150 ℃; for 0.0666667h; Microwave irradiation; Inert atmosphere;

Reference yield:

4-heptanone (123-19-3) → methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1109230-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 h / 20 °C

2.1: triethylamine / tetrahydrofuran / 4.17 h / 0 - 20 °C / Inert atmosphere

3.1: dmap; trifluoromethylsulfonic anhydride / dichloromethane / 20.75 h / 0 - 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 20 h / 70 °C

5.1: hydrogen / palladium / methanol / 2.33 h / 25 °C / 1500.15 Torr

6.1: n-Butyl nitrite / acetonitrile / 0.42 h / 0 °C

6.2: 4 h / 20 °C

7.1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.07 h / 150 °C / Microwave irradiation; Inert atmosphere

With dmap; n-Butyl nitrite; trifluoromethylsulfonic anhydride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

N-[2-(2-bromophenyl)ethyl]heptan-4-amine (1109229-81-3) → methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1109230-57-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran / 4.17 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; trifluoromethylsulfonic anhydride / dichloromethane / 20.75 h / 0 - 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 20 h / 70 °C

4.1: hydrogen / palladium / methanol / 2.33 h / 25 °C / 1500.15 Torr

5.1: n-Butyl nitrite / acetonitrile / 0.42 h / 0 °C

5.2: 4 h / 20 °C

6.1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.07 h / 150 °C / Microwave irradiation; Inert atmosphere

With dmap; n-Butyl nitrite; trifluoromethylsulfonic anhydride; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

(3‐cyanophenyl)boronic acid

4-heptanone

N-[2-(2-bromophenyl)ethyl]heptan-4-amine

Downstream raw materials:

7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide

N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride