methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

Base Information

• Chemical Name: methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS No.: 867313-44-8
• Molecular Formula: C₂₉H₂₅NO₉
• Molecular Weight: 531.519
• Mol file: 867313-44-8.mol

Synonyms:methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

Chemical Property of methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

There total 19 articles about methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-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: 86.0%

methyl 2-(2,4-diisopropoxy-5-methoxyphenyl)-8-isopropoxy-1-(4-isopropoxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate (867313-43-7) → methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate (867313-44-8)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 0.166667h; sonication;

DOI:10.1021/jm0602458

Reference yield:

1-bromo-2,4-bis(isopropyloxy)-5-methoxybenzene (867313-40-4) → methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate (867313-44-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Pd(PPh₃)4; aq. K₃PO₄ / dimethylformamide / 5 h / 115 °C

2: 95 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone / CHCl₃ / 0.17 h / 120 °C / microwave irradiation

3: 86 percent / AlCl₃ / CH₂Cl₂ / 0.17 h / sonication

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; N,N-dimethyl-formamide; 2: Suzuki cross-coupling;

DOI:10.1021/jm0602458

Reference yield:

methyl 8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate (850346-72-4) → methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate (867313-44-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / 70 °C

2: 92 percent / Pd(PPh₃)4; aq. K₂CO₃ / dimethylformamide / 14 h / 125 °C

3: 83 percent / K₂CO₃ / dimethylformamide / 17 h / 80 °C

4: 84 percent / N-bromosuccinimide / tetrahydrofuran / 1.5 h / 70 °C

5: 89 percent / Pd(PPh₃)4; aq. K₃PO₄ / dimethylformamide / 5 h / 115 °C

6: 95 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone / CHCl₃ / 0.17 h / 120 °C / microwave irradiation

7: 86 percent / AlCl₃ / CH₂Cl₂ / 0.17 h / sonication

With potassium phosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; 2: Suzuki cross-coupling / 5: Suzuki cross-coupling;

DOI:10.1021/jm0602458

upstream raw materials:

methyl 2-(2,4-diisopropoxy-5-methoxyphenyl)-8-isopropoxy-1-(4-isopropoxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

4-hydroxy-3-methoxyphenylboronic acid pinacol ester

methyl 1-[2-bromo-5-isopropoxy-4-methoxyphenethyl]-1H-pyrrole-2-carboxylate

methyl 8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Downstream raw materials:

lamellarin D