3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole

Base Information

• Chemical Name: 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole
• CAS No.: 911677-74-2
• Molecular Formula: C₃₅H₄₆BrN₃O₄SSi
• Molecular Weight: 712.823
• Mol file: 911677-74-2.mol

Synonyms:3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole

Chemical Property of 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole

There total 4 articles about 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole 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: 85.0%

2-bromo-5-iodo-6-methoxy-3-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazine (911677-73-1) + 3-(tributylstannyl)-1-(toluene-4-sulfonyl)-indole (156021-25-9) → 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole (911677-74-2)

Guidance literature:

With copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1021/ol0617547

Reference yield:

1-(3-bromo-6-iodo-5-methoxy-pyrazin-2-yl)-hex-5-en-1-ol (911677-86-6) → 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole (911677-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / imidazole / dimethylformamide / 16 h / 40 °C

2: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

With 1H-imidazole; copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dimethyl sulfoxide; N,N-dimethyl-formamide; 2: Stille coupling reaction;

DOI:10.1021/ol0617547

Reference yield:

hex-5-en-1-al (764-59-0) → 3-[5-bromo-3-methoxy-6-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazin-2-yl]-1-(toluene-4-sulfonyl)-1H-indole (911677-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

2: 86 percent / imidazole / dimethylformamide / 16 h / 40 °C

3: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

With 1H-imidazole; n-butyllithium; diisopropylamine; copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3: Stille coupling reaction;

DOI:10.1021/ol0617547

upstream raw materials:

2-bromo-5-iodo-6-methoxy-3-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazine

3-(tributylstannyl)-1-(toluene-4-sulfonyl)-indole

1-(3-bromo-6-iodo-5-methoxy-pyrazin-2-yl)-hex-5-en-1-ol

hex-5-en-1-al

Downstream raw materials:

{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid

{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid methyl ester

C₄₆H₅₆N₄O₈SSi

4-{3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-5H-cycloheptapyrazin-6-yl}-2,2-dimethyl-5-vinyl-oxazole-3-carboxylic acid tert-butyl ester