2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

Base Information

Chemical Name:2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine
CAS No.:1312016-74-2
Molecular Formula:C₂₃H₂₈N₂O₃S
Molecular Weight:412.553
Hs Code.:

Synonyms:2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

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Chemical Property of 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

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Technology Process of 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

There total 6 articles about 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-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:

2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine: 1312016-73-1
2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

: 1312016-74-2
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

: 1312021-11-6
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: With Daicel AD-H; In isopropyl alcohol; at 25 ℃; Resolution of racemate;

Reference yield:

: 36052-24-1
methyl 6-aminonicotinoate

: 1312016-74-2
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

: 1312021-11-6
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: Multi-step reaction with 16 steps

1.1: iodine; silver trifluoroacetate / methanol / 72 h / 25 °C

2.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2 h / 0 - 25 °C

3.1: pyridine / dichloromethane / 12 h / 0 - 25 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Reflux

5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C

5.2: 12.25 h / 0 - 25 °C

6.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 - 20 °C

7.1: thionyl chloride / dichloromethane / 2 h / 0 °C

8.1: methanol / 12 h / 20 °C

9.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C

9.2: 12.25 h / 0 - 25 °C

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

10.2: 1 h / -78 °C

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

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

12.2: 1.5 h / -78 °C

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

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

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

16.1: Daicel AD-H / isopropyl alcohol / 25 °C / Resolution of racemate

With pyridine; copper(l) iodide; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; iodine; silver trifluoroacetate; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

: 1312018-57-7
(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol

: 1312016-74-2
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

: 1312021-11-6
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: Multi-step reaction with 10 steps

1.1: thionyl chloride / dichloromethane / 2 h / 0 °C

2.1: methanol / 12 h / 20 °C

3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C

3.2: 12.25 h / 0 - 25 °C

4.1: n-butyllithium / hexane; 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 AD-H / isopropyl alcohol / 25 °C / Resolution of racemate

With n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium carbonate; Dess-Martin periodane; sodium hydroxide; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; isopropyl alcohol;