N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

Base Information

Chemical Name:N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine
CAS No.:178877-08-2
Molecular Formula:C₂₈H₂₉BrN₂O₃
Molecular Weight:521.454
Hs Code.:

Synonyms:N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

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Chemical Property of N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

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Technology Process of N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

There total 7 articles about N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-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:

: 870-63-3
prenyl bromide

: 178877-07-1
N-tert-butoxycarbonyl-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

: 178877-08-2
N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

Guidance literature:: With sodium hydride; Yield given. Multistep reaction; 1) DMF, 25 deg C, 30 min, 2) DMF, 0 deg C, 1 h; 25 deg C, overnight;
DOI:10.1021/jo9605298

Reference yield:

: 178876-99-8
7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester

: 178877-08-2
N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

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: 87 percent / NBS, H₂SO₄ / tetrahydrofuran / 4 h / -60 °C

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

With lithium hydroxide; N-Bromosuccinimide; sulfuric acid; diphenyl phosphoryl azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo9605298

Reference yield:

: 178877-00-4
4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester

: 178877-08-2
N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃ / ethanol / 1 h / Heating

2: 100 percent / K₂CO₃, Bu₄NI / dimethylformamide / 11 h / 25 °C

3: 96 percent / dimethylformamide / 20 h / Heating

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 h / 25 °C

5: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

6: 87 percent / NBS, H₂SO₄ / tetrahydrofuran / 4 h / -60 °C

7: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) DMF, 0 deg C, 1 h; 25 deg C, overnight

With lithium hydroxide; N-Bromosuccinimide; sulfuric acid; diphenyl phosphoryl azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo9605298