methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate

Base Information

• Chemical Name: methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate
• CAS No.: 736138-24-2
• Molecular Formula: C₃₀H₂₆ClN₃O₆
• Molecular Weight: 560.006
• Mol file: 736138-24-2.mol

Synonyms:methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate

Chemical Property of methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate

There total 6 articles about methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-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:

5-hydroxy-6-methoxyindole-2-carboxylic acid (2495-80-9) + 4-benzyloxy-8-chloromethyl-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester → methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate (736138-24-2)

Guidance literature:

With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1021/ja0472735

Reference yield:

5-benzyloxy-6-methoxy-1H-indole-2-carboxylic acid (2495-81-0) → methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate (736138-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

2: NaHCO₃; EDCI / dimethylformamide / 12 h / 25 °C

With hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0472735

Reference yield:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → methyl 3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrole[3,2-e]indole-7-carboxylate (736138-24-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / NaOMe / methanol / 27 h / -15 - 0 °C

2: 66 percent / xylene / 12 h / 130 °C

3: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 4 h / 25 °C

4: 83 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

5: NaHCO₃; EDCI / dimethylformamide / 12 h / 25 °C

With lithium hydroxide; hydrogen; sodium methylate; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; xylene;

DOI:10.1021/ja0472735

upstream raw materials:

5-hydroxy-6-methoxyindole-2-carboxylic acid

5-benzyloxy-6-methoxy-1H-indole-2-carboxylic acid

3-benzyloxy-4-methoxybenzaldehyde

methyl 5-benzyloxy-6-methoxy-1H-indole-2-carboxylate

Downstream raw materials:

3-[(5-hydroxy-6-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid