3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Base Information

Chemical Name:3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
CAS No.:1227611-85-9
Molecular Formula:C₂₁H₂₂BCl₂FN₂O₂
Molecular Weight:435.133
Hs Code.:

Synonyms:3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

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Chemical Property of 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

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Technology Process of 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

There total 10 articles about 3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-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:

: 1227611-88-2
5-bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

: 73183-34-3
bis(pinacol)diborane

: 1227611-85-9
3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield:

: 178813-78-0
2,6?dichloro?3?fluorobenzoic acid

: 1227611-85-9
3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: borane-THF / tetrahydrofuran / 12 h / Reflux

2.1: sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 0.5 h / -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: 4 h / -78 - 65 °C

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

6.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 0 °C

7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

With sodium hypochlorite; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride diethyl etherate; water; potassium acetate; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium bromide; potassium hydroxide; sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1227611-85-9
3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: Multi-step reaction with 5 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: 4 h / -78 - 65 °C

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

4.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 0 °C

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

With boron trifluoride diethyl etherate; water; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;