(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

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Chemical Name:(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone
CAS No.:404888-96-6
Molecular Formula:C₂₇H₂₀Br₂N₄O₃S
Molecular Weight:640.355
Hs Code.:

Synonyms:(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

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Chemical Property of (S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

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Technology Process of (S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

There total 10 articles about (S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 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: 82.0%

: 404888-95-5
(S)-N-[2-azido-2-(N-tosyl-6-bromo-indol-3-yl)ethyl]-2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide

: 404888-96-6
(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

Guidance literature:: With tributylphosphine; In toluene; for 20h; Heating;
DOI:10.1021/jo0108109

Reference yield:

: 108061-76-3
2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

: 404888-96-6
(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

Guidance literature:: Multi-step reaction with 2 steps

1: 490 mg / Et₃N / dimethylformamide / 4 h

2: 82 percent / tributylphosphine / toluene / 20 h / Heating

With tributylphosphine; triethylamine; In N,N-dimethyl-formamide; toluene; 2: Staudinger-Wittig cyclization;
DOI:10.1021/jo0108109

Reference yield:

: 354538-27-5
6-bromo-1-tosyl-3-vinyl-1H-indole

: 404888-96-6
(S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O

2: 75 percent / CH₂Cl₂ / 6 h / Heating

3: 80 percent / NaN₃ / dimethylformamide / 12 h / 80 °C

4: SnCl₂*2H₂O / methanol / 20 h / 30 °C

5: 600 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

6: 83 percent / diphenylphosphoryl azide; DEAD; PPh₃ / tetrahydrofuran / -20 - 20 °C

7: CF₃COOH / CH₂Cl₂ / 20 °C

8: 490 mg / Et₃N / dimethylformamide / 4 h

9: 82 percent / tributylphosphine / toluene / 20 h / Heating

With sodium azide; tributylphosphine; AD-mix-β; diphenylphosphoranyl azide; triethylamine; triphenylphosphine; trifluoroacetic acid; tin(ll) chloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Sharpless dihydroxylation / 6: Mitsunobu reaction / 9: Staudinger-Wittig cyclization;
DOI:10.1021/jo0108109