(S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate

Base Information

• Chemical Name: (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate
• CAS No.: 1421615-99-7
• Molecular Formula: C₂₂H₂₂F₃NO₃
• Molecular Weight: 405.417

Synonyms:(S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate

Chemical Property of (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate

There total 6 articles about (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-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: 70.0%

(S)-tert-butyl 2,2,2-trifluoro-1-(2-((3-methoxyphenyl)ethynyl)phenyl)ethylcarbamate (1421615-60-2) → (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-99-7) + (S,Z)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-84-0) + (S)-tert-butyl 3-(3-methoxyphenyl)-1-(trifluoromethyl)isoquinoline-2(1H)-carboxylate (1421616-04-7)

Guidance literature:

With (triphenylphosphine)gold(I) chloride; ethanol; (SPhos)AuNTf₂; In ethanol; 1,2-dichloro-ethane; at 40 ℃; Inert atmosphere;

DOI:10.1021/ol3035142

Reference yield:

(S)-(+)-N-(2-iodobenzylidene)-2-methylpropane-2-sulfinamide → (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-99-7) + (S,Z)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-84-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutylammonium acetate / tetrahydrofuran / -20 °C / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane; methanol / 0.33 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / 1,4-dioxane / 20 °C / Inert atmosphere

4.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

4.2: 6 h / Inert atmosphere; Heating

5.1: (triphenylphosphine)gold(I) chloride; (SPhos)AuNTf₂; ethanol / 1,2-dichloro-ethane; ethanol / 40 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; (triphenylphosphine)gold(I) chloride; ethanol; (SPhos)AuNTf₂; tetrabutylammonium acetate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; 1,2-dichloro-ethane; 4.2: |Sonogashira Cross-Coupling;

DOI:10.1021/ol3035142

Reference yield:

2-iodobenzaldehyde (26260-02-6) → (S,E)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-99-7) + (S,Z)-tert-butyl 1-(3-methoxybenzylidene)-3-(trifluoromethyl)isoindoline-2-carboxylate (1421615-84-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 0.08 h / Inert atmosphere

1.2: 20 h / 20 °C / Inert atmosphere

2.1: tetrabutylammonium acetate / tetrahydrofuran / -20 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane; methanol / 0.33 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / 1,4-dioxane / 20 °C / Inert atmosphere

5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

5.2: 6 h / Inert atmosphere; Heating

6.1: (triphenylphosphine)gold(I) chloride; (SPhos)AuNTf₂; ethanol / 1,2-dichloro-ethane; ethanol / 40 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; titanium(IV) tetraethanolate; (triphenylphosphine)gold(I) chloride; ethanol; (SPhos)AuNTf₂; tetrabutylammonium acetate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; 5.2: |Sonogashira Cross-Coupling;

DOI:10.1021/ol3035142

upstream raw materials:

(S)-tert-butyl [2,2,2-trifluoro-1-(2-iodophenyl)ethyl]carbamate

(S)-tert-butyl 2,2,2-trifluoro-1-(2-((3-methoxyphenyl)ethynyl)phenyl)ethylcarbamate

(R)-2-methyl-N-[(S)-2,2,2-trifluoro-1-(2-iodophenyl)ethyl]propane-2-sulfinamide

2-iodobenzaldehyde

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