3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran

Base Information

• Chemical Name: 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran
• CAS No.: 153001-69-5
• Molecular Formula: C₂₄H₂₄BrNO₄
• Molecular Weight: 470.363
• Mol file: 153001-69-5.mol

Synonyms:3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran

Chemical Property of 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran

There total 10 articles about 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran 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: 96.0%

propargyl bromide (106-96-7) + 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)amino)-7-(benzyloxy)benzofuran (153001-68-4) → 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran (153001-69-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; toluene; for 3h; Ambient temperature;

DOI:10.1021/jm00028a005

Reference yield:

potassium 2-methoxy-4-nitrophenolate monohydrate (100200-99-5) → 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran (153001-69-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / KI / acetone; H₂O / 24 h / Heating

2: 56 percent / toluene / 8 h / 180 °C

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 30 min

4: polyphosphoric acid / benzene / 6 h / Heating

5: 24.3 g / pyridinium hydrochloride / 2 h / 170 °C

6: NaH / dimethylformamide / 5 h / 24 °C

7: H₂ / PtO₂ / ethyl acetate / 1.5 h / 1034.3 Torr

8: dioxane / 3 h / Heating

9: 92 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 5 h / -61 °C

10: 96 percent / NaH / toluene; dimethylformamide / 3 h / Ambient temperature

With N-Bromosuccinimide; PPA; dimethylsulfide; sulfuric acid; hydrogen; pyridine hydrochloride; sodium hydride; ozone; potassium iodide; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/jm00028a005

Reference yield:

3-Methyl-5-nitro-benzofuran-7-ol (1026597-26-1) → 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran (153001-69-5)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 5 h / 24 °C

2: H₂ / PtO₂ / ethyl acetate / 1.5 h / 1034.3 Torr

3: dioxane / 3 h / Heating

4: 92 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 5 h / -61 °C

5: 96 percent / NaH / toluene; dimethylformamide / 3 h / Ambient temperature

With N-Bromosuccinimide; sulfuric acid; hydrogen; sodium hydride; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00028a005

upstream raw materials:

propargyl bromide

3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)amino)-7-(benzyloxy)benzofuran

potassium 2-methoxy-4-nitrophenolate monohydrate

3-Methyl-5-nitro-benzofuran-7-ol

Downstream raw materials:

(+)-(1R)-1,2-dihydro-1-(hydroxymethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-8-methyl-3H-furano<3,2-e>indole

(+)-(1R)-1,2-dihydro-1-(chloromethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-8-methyl-3H-furano<3,2-e>indole

4-Benzyloxy-1-methyl-8-methylene-7,8-dihydro-furo[3,2-e]indole-6-carboxylic acid tert-butyl ester