3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid

Base Information

• Chemical Name: 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid
• CAS No.: 1313803-03-0
• Molecular Formula: C₂₅H₁₇F₃N₄O₂S
• Molecular Weight: 494.497

Synonyms:3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid

Chemical Property of 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid

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Technology Process of 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid

There total 5 articles about 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid 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: 38.0%

5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophene-2-carbaldehyde (1595282-85-1) + meta-aminobenzoic acid (99-05-8,159139-79-4) → 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid (1313803-03-0)

Guidance literature:

With sodium cyanoborohydride; toluene-4-sulfonic acid; In methanol; dichloromethane; at 25 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bmc.2014.02.024

Reference yield:

4-trifluoromethylphenylboronic acid (128796-39-4) → 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid (1313803-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 24 h / 100 °C / Inert atmosphere

2: copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; potassium phosphate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere

3: toluene-4-sulfonic acid; sodium cyanoborohydride / dichloromethane; methanol / 24 h / 25 °C / Inert atmosphere

With potassium phosphate; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; trans-N,N'-dimethylcyclohexane-1,2-diamine; In 1,4-dioxane; methanol; dichloromethane; water; 1: |Suzuki Coupling / 2: |Buchwald Indole Synthesis;

DOI:10.1016/j.bmc.2014.02.024

Reference yield:

4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 3-((5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophen-2-yl)methylamino)benzoic acid (1313803-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 24 h / 100 °C / Inert atmosphere

2: copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; potassium phosphate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere

3: toluene-4-sulfonic acid; sodium cyanoborohydride / dichloromethane; methanol / 24 h / 25 °C / Inert atmosphere

With potassium phosphate; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; trans-N,N'-dimethylcyclohexane-1,2-diamine; In 1,4-dioxane; methanol; dichloromethane; water; 1: |Suzuki Coupling / 2: |Buchwald Indole Synthesis;

DOI:10.1016/j.bmc.2014.02.024

upstream raw materials:

4-trifluoromethylphenylboronic acid

5-(4-(4-(trifluoromethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)thiophene-2-carbaldehyde

meta-aminobenzoic acid

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

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