2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde

Base Information

• Chemical Name: 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde
• CAS No.: 476623-24-2
• Molecular Formula: C₄₄H₄₅BrN₄O₆SSi
• Molecular Weight: 865.92
• Mol file: 476623-24-2.mol

Synonyms:2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde

Chemical Property of 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde

There total 16 articles about 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde 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:

2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propan-1-ol → 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde (476623-24-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 0.333333h;

DOI:10.1021/ja027822b

Reference yield:

6-bromo-1H-indole (52415-29-9) → 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde (476623-24-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h

2.1: perchloric acid; mercury(II) diacetate; acetic acid / 24 h

2.2: BH₃*THF / 1 h / 23 °C

2.3: water

3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 72 h / 23 °C

4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 72 h / 50 °C

5.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 0 °C

6.1: Dess-Martin periodane / dichloromethane / 0.33 h / 23 °C

With potassium hydroxide; perchloric acid; mercury(II) diacetate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene; 3.1: Suzuki coupling / 4.1: Suzuki coupling;

DOI:10.1021/ja027822b

Reference yield:

1-(benzyloxy)-4-bromo-2-nitrobenzene (383868-64-2) → 2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionaldehyde (476623-24-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 4 h / -40 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 23 °C

2.2: 13 / 6 h / 23 °C

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: 13; 17 / 1.5 h / -78 °C

4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 2 h / 80 °C

5.1: hydrogen / palladium / benzene / 1 h / 760.05 Torr

6.1: N-Bromosuccinimide / tetrahydrofuran / 0.08 h

7.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

7.2: 13; 17 / 1 h / -78 °C

8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 72 h / 50 °C

9.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 0 °C

10.1: Dess-Martin periodane / dichloromethane / 0.33 h / 23 °C

With N-Bromosuccinimide; hydrogen; tert.-butyl lithium; sodium hydride; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; methanol; dichloromethane; pentane; benzene; 4.1: Suzuki coupling / 8.1: Suzuki coupling;

DOI:10.1021/ja027822b

upstream raw materials:

6-bromo-1H-indole

1-(benzyloxy)-4-bromo-2-nitrobenzene

5-bromo-3-methoxypyrazin-2-amine

6-bromo-1-(4-methylphenylsulfonyl)-1H-indole

Downstream raw materials:

2-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-propionic acid

1-amino-3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-butan-2-one

3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-1-nitro-butan-2-one

3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-1-bromo-butan-2-one