{4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene

Base Information

• Chemical Name: {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene
• CAS No.: 218912-13-1
• Molecular Formula: C₁₈H₂₈Br₂N₆OSi
• Molecular Weight: 532.353

Synonyms:{4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene

Chemical Property of {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene

There total 9 articles about {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene 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: 79.0%

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (218912-12-0) → {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene (218912-13-1)

Guidance literature:

With diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene (218912-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

2.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

3.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

4.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

5.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

6.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

7.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; AD-α; diphenylphosphoranyl azide; water; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Reduction / 2.1: Diazotization / 2.2: Substitution / 3.1: Oxidation / 4.1: Condensation / 5.1: Addition / 6.1: Etherification / 7.1: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → {4-[1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,6-dibromo-phenyl}-pyrrolidin-1-yl-diazene (218912-13-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / SOCl₂ / 2 h / Heating

2.1: 98 percent / Br₂; AcOH / 0.5 h / 25 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

4.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

5.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

6.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

7.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

8.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

9.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; AD-α; diphenylphosphoranyl azide; water; bromine; acetic acid; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Bromination / 3.1: Reduction / 4.1: Diazotization / 4.2: Substitution / 5.1: Oxidation / 6.1: Condensation / 7.1: Addition / 8.1: Etherification / 9.1: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

methyl 3,5-dibromo-4-aminobenzoate

4-amino-benzoic acid

4-methoxycarbonyl aniline

Downstream raw materials:

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine

tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid

(R)-2-Amino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

{1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester

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