(R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide

Base Information

• Chemical Name: (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide
• CAS No.: 1596347-26-0
• Molecular Formula: C₃₁H₃₄N₂O₈
• Molecular Weight: 562.62
• Mol file: 1596347-26-0.mol

Synonyms:

Chemical Property of (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide

There total 7 articles about (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide 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: 31.0%

(R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-9-iodo-4-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide (1596347-20-4) + 4-methoxyphenylboronic acid (5720-07-0) → (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide (1596347-26-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; water; at 100 ℃; for 1h; Microwave irradiation; Inert atmosphere;

DOI:10.1002/cmdc.201300395

Reference yield:

(5R)-5-((1S)-4,5-dimethoxy-1,3-dihydro-2-benzofuran-1-yl)-4-methoxy-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline (488720-99-6) → (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide (1596347-26-0)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid; N-iodo-succinimide / 2 h / -5 - 20 °C

2: hydrogenchloride / water

3: acetonitrile / 2 h / -5 - 20 °C / Inert atmosphere

4: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 1 h / 100 °C / Microwave irradiation; Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; water; acetonitrile; 4: |Suzuki Coupling;

DOI:10.1002/cmdc.201300395

Reference yield:

(3S)-6,7-dimethoxy-3-((R)-4-methoxy-5,6,7,8-tetrahydro-[1,3]dioxolo [4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one (92621-03-9,36017-64-8) → (R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-4-methoxy-9-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide (1596347-26-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 24 h / -5 - 20 °C

1.2: 1 h

2.1: trifluoroacetic acid; N-iodo-succinimide / 2 h / -5 - 20 °C

3.1: hydrogenchloride / water

4.1: acetonitrile / 2 h / -5 - 20 °C / Inert atmosphere

5.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 1 h / 100 °C / Microwave irradiation; Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-iodo-succinimide; boron trifluoride diethyl etherate; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; water; acetonitrile; 5.1: |Suzuki Coupling;

DOI:10.1002/cmdc.201300395

upstream raw materials:

(R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-N-ethyl-9-iodo-4-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxamide

4-methoxyphenylboronic acid

α-narcotine N-oxide

noscapine