methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Base Information

• Chemical Name: methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate
• CAS No.: 227084-67-5
• Molecular Formula: C₂₆H₂₇ClN₂O₅
• Molecular Weight: 482.964
• Mol file: 227084-67-5.mol

Synonyms:methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Chemical Property of methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

There total 14 articles about methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-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: 87.0%

methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate (280573-11-7) → methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate (227084-67-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 70 ℃; for 3h;

DOI:10.1021/jo000177b

Reference yield: 73.0%

methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate (280573-03-7) → methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate (227084-67-5)

Guidance literature:

With tetrachloromethane; triphenylphosphine; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/jo000177b

Reference yield:

methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate (227084-56-2) → methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate (227084-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaH / dimethylformamide / 12 h / 25 °C

2: 87 percent / Bu₃SnH; AIBN / benzene / 3 h / 70 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In N,N-dimethyl-formamide; benzene; 1: Alkylation / 2: Cyclization;

DOI:10.1021/jo000177b

upstream raw materials:

methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate

methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

di-tert-butyl dicarbonate

benzyl bromide

Downstream raw materials:

(S)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylic acid