(Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Base Information

• Chemical Name: (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
• CAS No.: 1293387-89-9
• Molecular Formula: C₂₀H₁₉FN₂O₃
• Molecular Weight: 354.381

Synonyms:(Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Chemical Property of (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

There total 8 articles about (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-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%

methyl 1-(4-fluorobenzyl)-4-(trifluoromethylsulfonyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (868551-52-4) + tributyl-((Z)-2-ethoxy-vinyl)-stannane (64724-29-4) → (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1293387-89-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; lithium chloride; In N,N-dimethyl-formamide; at 60 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jm200208d

Reference yield:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (936-12-9) → (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1293387-89-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / Inert atmosphere

1.2: 16.75 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / ethyl acetate / 1.75 h / 20 °C

2.2: 1.5 h / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

3.2: 17 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 2068.65 Torr / Inert atmosphere

6.1: triethylamine / dichloromethane / 0 °C

7.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7.1: Stille coupling;

DOI:10.1021/jm200208d

Reference yield:

ethyl 1-(4-fluorobenzyl)-2-methyl-1H-pyrrole-3-carboxylate (868551-47-7) → (Z)-methyl 4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1293387-89-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-Bromosuccinimide / ethyl acetate / 1.75 h / 20 °C

1.2: 1.5 h / Reflux

2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

2.2: 17 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 2068.65 Torr / Inert atmosphere

5.1: triethylamine / dichloromethane / 0 °C

6.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Stille coupling;

DOI:10.1021/jm200208d

upstream raw materials:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

ethyl 1-(4-fluorobenzyl)-2-methyl-1H-pyrrole-3-carboxylate

ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate

ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

Downstream raw materials:

7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

3-(4-fluorobenzyl)-7-hydroxy-N,N-dimethyl-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c]-1,7-naphthyridine-1-sulfonamide p-toluenesulfonic acid salt

3-(4-fluorobenzyl)-1-[ (4-methylpiperidin-1-yl)sulfonyl]-7-(tetrahydro-2H-pyran-2-yloxy)-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c][ 1,7]naphthyridin-6-one

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