N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

Base Information

Chemical Name:N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide
CAS No.:869586-56-1
Molecular Formula:C₁₉H₂₀BrN₃O₆S₂
Molecular Weight:530.42
Hs Code.:

Synonyms:N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

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Chemical Property of N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

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Technology Process of N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

There total 10 articles about N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide 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: 97.0%

: 869586-25-4
6-bromo-5-methoxy-3-{2-[methylsulfanyloxymethoxy-(2-nitrobenzenesulfonyl)-amino]ethyl}-indole-1-carboxylic acid tert-butyl ester

: 869586-56-1
N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

Guidance literature:: With dimethylsulfide; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ja055832h

Reference yield:

: 5-bromo-2-iodo-4-methoxyaniline

: 869586-56-1
N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 0 °C

2: 5.65 g / PPh₃; DEAD / benzene; toluene / 5 - 20 °C

3: 66 percent / Pd(OAc)2; benzyltriethylammonium chloride; Et₃N / dimethylformamide / 0.5 h / 80 °C

4: 100 percent / DMAP / CH₂Cl₂ / 0.33 h / 20 °C

5: 97 percent / CSA / methanol / 0.5 h / 20 °C

6: 100 percent / PPh₃; DEAD / benzene; toluene / 0.25 h / 20 °C

7: 97 percent / dimethyl sulfide; TFA / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; palladium diacetate; dimethylsulfide; camphor-10-sulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 2: Mitsunobu reaction / 3: Heck reaction / 6: Mitsunobu reaction;
DOI:10.1021/ja055832h

Reference yield:

: 1361021-39-7
1-bromo-4-iodo-2-methoxy-5-nitrobenzene

: 869586-56-1
N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1: Fe; FeCl₂; aq. HCl / ethanol / 2 h / 80 °C

2: pyridine / CH₂Cl₂ / 0 °C

3: 5.65 g / PPh₃; DEAD / benzene; toluene / 5 - 20 °C

4: 66 percent / Pd(OAc)2; benzyltriethylammonium chloride; Et₃N / dimethylformamide / 0.5 h / 80 °C

5: 100 percent / DMAP / CH₂Cl₂ / 0.33 h / 20 °C

6: 97 percent / CSA / methanol / 0.5 h / 20 °C

7: 100 percent / PPh₃; DEAD / benzene; toluene / 0.25 h / 20 °C

8: 97 percent / dimethyl sulfide; TFA / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; hydrogenchloride; dmap; palladium diacetate; dimethylsulfide; camphor-10-sulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; iron; triethylamine; triphenylphosphine; trifluoroacetic acid; iron(II) chloride; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3: Mitsunobu reaction / 4: Heck reaction / 7: Mitsunobu reaction;
DOI:10.1021/ja055832h