3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate

Base Information

• Chemical Name: 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate
• CAS No.: 539856-46-7
• Molecular Formula: C₃₀H₃₅ClN₂O₇
• Molecular Weight: 571.07
• Mol file: 539856-46-7.mol

Synonyms:3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate

Chemical Property of 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate

There total 16 articles about 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate 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: 79.0%

methyl (E/Z)-7-(benzyloxy)-4-bromo-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)(3'-chloroprop-2'-enyl)amino]indole-2-carboxylate (539856-45-6) → 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate (539856-46-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In benzene; at 80 ℃; for 3h;

DOI:10.1002/ejoc.200390094

Reference yield: 70.0%

1-(1,1-dimethylethyl)-2-methyl 5-[(3-chloro-2-propenyl)-(1,1-dimethylethoxy)carbonylamino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate (919535-10-7) → 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate (539856-46-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In toluene; at 90 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01373

Reference yield:

1-(1,1-dimethylethyl)-2-methyl-5-nitro-6-(phenylmethoxy)-indole-1,2-dicarboxylate (539856-49-0) → 3.6-bis(1,1-dimethylethyl)-2-methyl 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)benzo[1,2-b:4,3-b′]dipyrrole-2,3,6-tricarboxylate (539856-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / quinoline; hydrogen / Lindlar catalyst / ethyl acetate / 16 h / 20 °C

2.1: 89 percent / tetrahydrofuran / 18 h / 20 °C

3.1: 89 percent / N-bromosuccinimide / tetrahydrofuran / 4 h / -78 °C

4.1: NaH / dimethylformamide; light petroleum / 0.5 h / 20 °C

4.2: 92 percent / dimethylformamide; light petroleum / 12 h / 20 °C

5.1: 79 percent / tris(trimethylsilyl)silane; AIBN / benzene / 3 h / 80 °C

With quinoline; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; hydrogen; sodium hydride; Lindlar's catalyst; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether; benzene;

DOI:10.1002/ejoc.200390094

upstream raw materials:

methyl (E/Z)-7-(benzyloxy)-4-bromo-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)(3'-chloroprop-2'-enyl)amino]indole-2-carboxylate

di-tert-butyl dicarbonate

benzyl bromide

methyl 7-hydroxy-5-nitro-1H-indole-2-carboxylate

Downstream raw materials:

methyl (1R/S)-5-benzyloxy-1-(chloromethyl)-3-[(5,6,7-trimethoxyindole-2-yl)carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

methyl (1R/S)-1-(chloromethyl)-5-hydroxy-3-[(5,6,7-trimethoxyindole-2-yl)carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate