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

Base Information

• Chemical Name: 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one
• CAS No.: 476623-27-5
• Molecular Formula: C₃₂H₂₆BrN₅O₅
• Molecular Weight: 640.493

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

Chemical Property of 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one

Chemical Property:

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Technology Process of 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one

There total 20 articles about 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one 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:

3-[7-benzyloxy-3-[5-(6-bromo-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-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one (476623-27-5)

Guidance literature:

3-[7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-1-nitro-butan-2-one; With lithium tetrafluoroborate; water; In acetonitrile; at 70 ℃; for 1.5h;

With sodium hydroxide; In acetonitrile; at 40 ℃; for 0.166667h; Further stages.;

DOI:10.1021/ja027822b

Reference yield:

6-bromo-1H-indole (52415-29-9) → 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one (476623-27-5)

Guidance literature:

Multi-step reaction with 10 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

7.1: triethylamine / 15 h / 23 °C

8.1: Dess-Martin periodane / dichloromethane / 0.08 h / 23 °C

9.1: potassium hydroxide / ethanol / 2 h / 40 °C

10.1: lithium tetrafluoroborate; water / acetonitrile / 1.5 h / 70 °C

10.2: aq. NaOH / 7 / 0.17 h / 40 °C

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

DOI:10.1021/ja027822b

Reference yield:

1-(benzyloxy)-4-bromo-2-nitrobenzene (383868-64-2) → 3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one (476623-27-5)

Guidance literature:

Multi-step reaction with 14 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

11.1: triethylamine / 15 h / 23 °C

12.1: Dess-Martin periodane / dichloromethane / 0.08 h / 23 °C

13.1: potassium hydroxide / ethanol / 2 h / 40 °C

14.1: lithium tetrafluoroborate; water / acetonitrile / 1.5 h / 70 °C

14.2: aq. NaOH / 7 / 0.17 h / 40 °C

With potassium hydroxide; N-Bromosuccinimide; lithium tetrafluoroborate; water; hydrogen; tert.-butyl lithium; sodium hydride; sodium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 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

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