(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

Base Information

Chemical Name:(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide
CAS No.:1073616-24-6
Molecular Formula:C₂₀H₁₉ClF₃N₃O₃
Molecular Weight:441.837
Hs Code.:

Synonyms:(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

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Chemical Property of (S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

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Technology Process of (S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

There total 12 articles about (S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide 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: 56.0%

: 1073617-86-3
(S)-1-(3-chloro-1',2',3',6'-tetrahydro-[2,4']bipyridinyl-5-yl)ethane-1,2-diol

: 1548-13-6
p-trifluoromethyl-phenylisocyanate

: 1073616-24-6
(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

Guidance literature:: (S)-1-(3-chloro-1',2',3',6'-tetrahydro-[2,4']bipyridinyl-5-yl)ethane-1,2-diol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 0.166667h;

p-trifluoromethyl-phenylisocyanate; In dichloromethane; at -10 ℃; for 0.25h;

Reference yield: 56.0%

: (S)-1-(3-chloro-1′2',3',6'-tetrahydro-[2,4']bipyridinyl-5-yl)ethane-1,2-diol hydrochloride

: 1548-13-6
p-trifluoromethyl-phenylisocyanate

: 1073616-24-6
(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jm500818a

Reference yield:

: 71690-05-6
5,6-dichloro-pyridine-3-carbaldehyde

: 1073616-24-6
(S)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: Methyltriphenylphosphonium bromide; potassium tert-butylate / toluene; tetrahydrofuran / 1 h / 100 °C / Inert atmosphere

2.1: AD-mix-α / tert-butyl alcohol; water / 24 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h / Inert atmosphere

3.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,2-dimethoxyethane; ethanol; water / 2 h / 90 °C / Inert atmosphere

4.1: hydrogenchloride / dichloromethane; diethyl ether / 20 h / 0 °C / Inert atmosphere; Heating

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; AD-mix-α; potassium tert-butylate; Methyltriphenylphosphonium bromide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 3.1: |Suzuki Coupling;
DOI:10.1021/jm500818a