3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1227611-56-4
• Molecular Formula: C₂₀H₁₈Cl₂FN₃
• Molecular Weight: 390.287
• Mol file: 1227611-56-4.mol

Synonyms:3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property of 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

There total 10 articles about 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine 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:

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (885693-20-9) + ((S)-1-{5-bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester (1227611-86-0) → 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (1227611-56-4)

Guidance literature:

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester; ((S)-1-{5-bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester; With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 100 ℃; for 0.5h; Microwave irradiation;

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20 ℃; for 2h;

Reference yield:

2,6-dichloro-3-fluorobenzaldehyde (178813-77-9) → 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (1227611-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide / methanol / 0 - 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.17 h / -78 °C

2.2: 20 - 65 °C

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.5 h / 100 °C / Microwave irradiation

4.2: 2 h / 20 °C

With boron trifluoride diethyl etherate; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 4.1: Suzuki Coupling;

Reference yield:

2,6?dichloro?3?fluorobenzoic acid (178813-78-0) → 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (1227611-56-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: borane-THF / tetrahydrofuran / 20 °C / Reflux

2.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide / dichloromethane; water / -7 - -2 °C

3.1: potassium hydroxide / methanol / 0 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.17 h / -78 °C

4.2: 20 - 65 °C

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

6.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.5 h / 100 °C / Microwave irradiation

6.2: 2 h / 20 °C

With sodium hypochlorite; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride diethyl etherate; sodium hydrogencarbonate; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium bromide; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 6.1: Suzuki Coupling;

upstream raw materials:

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

((S)-1-{5-bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester

2,6-dichloro-3-fluorobenzaldehyde

2,6?dichloro?3?fluorobenzoic acid

Downstream raw materials:

5-{3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

Refernces