4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester

Base Information

• Chemical Name: 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester
• CAS No.: 1312019-79-6
• Molecular Formula: C₂₂H₂₁FN₂O₂
• Molecular Weight: 364.419
• Mol file: 1312019-79-6.mol

Synonyms:4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester

Chemical Property of 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester

There total 8 articles about 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester 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:

4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-3-fluoro-benzoic acid methyl ester (1312019-78-5) → 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester (1312019-79-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 16h;

Reference yield:

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (143141-23-5) → 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester (1312019-79-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C

1.2: 1 h / -78 °C

2.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

3.2: 1.5 h / -78 °C

4.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 25 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium carbonate; Dess-Martin periodane; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water;

Reference yield:

methyl 4-bromo-3-fluorobenzoate (849758-12-9) → 4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-3-fluoro-benzoic acid methyl ester (1312019-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

2: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 25 °C

With tetrabutyl ammonium fluoride; potassium acetate; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide;

upstream raw materials:

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

methyl 4-bromo-3-fluorobenzoate

cyclopentanealdehyde

methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Downstream raw materials:

2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-phenyl}-propan-2-ol

4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-benzoic acid methyl ester