(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

Base Information

Chemical Name:(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate
CAS No.:1392127-50-2
Molecular Formula:C₃₅H₄₃NO₆Si
Molecular Weight:601.815
Hs Code.:

Synonyms:(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

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Chemical Property of (E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

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Technology Process of (E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

There total 21 articles about (E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate 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: 98.0%

: 1392127-48-8
(E)-methyl 5-(tert-butyldimethylsilyloxy)-4-(5-hydroxy-2-oxopent-3-enyl)-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

: 98-88-4
benzoyl chloride

: 1392127-50-2
(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: With 2,4,6-trimethyl-pyridine; In acetonitrile; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol301424h

Reference yield:

: 949035-05-6
4-bromo-3-acetyl-1-methyl-1H-indole

: 1392127-50-2
(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

3: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; sodium t-butanolate / toluene / 0.42 h / 20 °C / Reflux; Inert atmosphere

4: sodium hydride / tetrahydrofuran; mineral oil / 41 h / 20 °C / Inert atmosphere

5: pyridine; N-Bromosuccinimide / water; N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere

6: borane tert-butylamine / tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere

7: 2,4,6-trimethyl-pyridine / acetonitrile / 2 h / 0 °C / Inert atmosphere

With pyridine; 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; borane tert-butylamine; sodium t-butanolate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol301424h

Reference yield:

: 1441119-24-9
C₁₂H₁₄BrNO

: 1392127-50-2
(E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

2: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; sodium t-butanolate / toluene / 0.42 h / 20 °C / Reflux; Inert atmosphere

3: sodium hydride / tetrahydrofuran; mineral oil / 41 h / 20 °C / Inert atmosphere

4: pyridine; N-Bromosuccinimide / water; N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere

5: borane tert-butylamine / tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere

6: 2,4,6-trimethyl-pyridine / acetonitrile / 2 h / 0 °C / Inert atmosphere

With pyridine; 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; borane tert-butylamine; sodium t-butanolate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol301424h