N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

Base Information

• Chemical Name: N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine
• CAS No.: 178877-18-4
• Molecular Formula: C₂₆H₂₅IN₂O₃
• Molecular Weight: 540.401
• Mol file: 178877-18-4.mol

Synonyms:N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

Chemical Property of N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

There total 8 articles about N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine 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:

sodium hydrogencarbonate (144-55-8) + allyl bromide (106-95-6) + N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-17-3) → N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-18-4)

Guidance literature:

With NaH; In N,N-dimethyl-formamide;

Reference yield:

allyl bromide (106-95-6) + N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-17-3) → N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-18-4)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) DMF, 0 deg C, 30 min, 2) DMF, 25 deg C, 2 h;

DOI:10.1021/jo9605298

Reference yield:

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester (178876-99-8) → N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-18-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / K₂CO₃, Bu₄NI / dimethylformamide / 11 h / 25 °C

2: 96 percent / dimethylformamide / 20 h / Heating

3: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 h / 25 °C

4: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

5: 68 percent / NIS, TsOH*H₂O / tetrahydrofuran; methanol / 1) -40 deg C, 1 h, 2) 25 deg C, 1 h

6: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) DMF, 25 deg C, 2 h

With lithium hydroxide; N-iodo-succinimide; diphenyl phosphoryl azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9605298

upstream raw materials:

allyl bromide

N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester

4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester

Downstream raw materials:

5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole

(+)-(1R)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

(-)-(1S)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

rac-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole