(R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide

Base Information

• Chemical Name: (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide
• CAS No.: 354538-23-1
• Molecular Formula: C₂₇H₂₀Br₂N₆O₄S
• Molecular Weight: 684.368

Synonyms:(R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide

Chemical Property of (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide

There total 13 articles about (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide 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:

6-bromo-1H-indole (52415-29-9) → (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide (354538-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / diethyl ether / 10 h / Heating

2: 107 mg / Et₃N / dimethylformamide / 4 h / 20 °C

With triethylamine; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo010265b

Reference yield:

6-bromo-1H-indole-3-carbaldehyde (17826-04-9) → (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide (354538-23-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / K₂CO₃ / butan-2-one / 3 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C

3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 12.5 h / 0 - 20 °C

5.1: 87 percent / Ph₃P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C

6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 4 h / 0 °C

9.1: 335 mg / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

10.1: 88 percent / NaN₃ / dimethylformamide / 12 h / 80 °C

11.1: CF₃CO₂H / CH₂Cl₂ / 20 °C

12.1: 107 mg / Et₃N / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; sodium azide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; tert-butyl alcohol; 2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo010265b

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide (354538-23-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / K₂CO₃ / butan-2-one / 3 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C

3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 12.5 h / 0 - 20 °C

5.1: 87 percent / Ph₃P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C

6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 4 h / 0 °C

9.1: 335 mg / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

10.1: 88 percent / NaN₃ / dimethylformamide / 12 h / 80 °C

11.1: CF₃CO₂H / CH₂Cl₂ / 20 °C

12.1: 107 mg / Et₃N / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; sodium azide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; tert-butyl alcohol; 2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo010265b

upstream raw materials:

6-bromo-1H-indole

6-bromo-1H-indole-3-carbaldehyde

p-toluenesulfonyl chloride

6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde

Downstream raw materials:

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

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