5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1312021-10-5
• Molecular Formula: C₂₂H₂₃F₃N₂O₂
• Molecular Weight: 404.432

Synonyms:5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

Chemical Property of 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

Purity/Quality:

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Technology Process of 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

There total 14 articles about 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-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-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312016-61-7) → 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(R)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312016-63-9) + 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312021-10-5)

Guidance literature:

With Daicel IB-H; In hexanes; ethanol; at 25 ℃; Resolution of racemate;

Reference yield:

ethyl tetrahydro-4H-pyran-4-ylideneacetate (130312-00-4) → 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(R)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312016-63-9) + 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312021-10-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol / 20 h / 25 °C / 1551.49 Torr

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux

2.2: 0 °C

3.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C

4.2: 1 h / -78 °C

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

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

6.2: 1.5 h / -78 °C

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

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

9.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr

10.1: Daicel IB-H / ethanol; hexanes / 25 °C / Resolution of racemate

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; Dess-Martin periodane; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water;

Reference yield:

ethyl tetrahydropyran-4-acetate (103260-44-2) → 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(R)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312016-63-9) + 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1(S)-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (1312021-10-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux

1.2: 0 °C

2.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C

3.2: 1 h / -78 °C

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

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

5.2: 1.5 h / -78 °C

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

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

8.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr

9.1: Daicel IB-H / ethanol; hexanes / 25 °C / Resolution of racemate

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; Dess-Martin periodane; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water;

upstream raw materials:

2-(tetrahydropyran-4-yl)-ethanol

ethyl tetrahydro-4H-pyran-4-ylideneacetate

ethyl tetrahydropyran-4-acetate

5-bromo-1H-pyrrolo[2,3-b]pyridine

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