7-chloro-2-((1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)quinoxaline → 7-chloro-2-(2-(1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethyl)quinoxaline

HRID 1055029Notes

Reaction equation

HRID 1055029 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([C:12]#[C:13][C:14]3[N:18]=[C:17]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:16]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[N:15]=3)=[N:9]2)=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[N:18]=[C:17]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)[N:16]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)[N:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 900174367-chloro-2-((1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)quinoxaline

Product 1

HCID 900172007-chloro-2-(2-(1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethyl)quinoxalineYield 51.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-chloro-2-((1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)quinoxaline (33 mg, 74.2 μmol, Eq: 1.00) was stirred in ethyl acetate (12 ml) with palladium, 5 wt % on barium sulfate, reduced (33.0 mg, 310 μmol, Eq: 4.18) under a hydrogen atmosphere for 2.5 h. Then 3 drops of acetic acid were added and stirring was continued for 1.5 h. The crude material was applied on silica gel and purified by column chromatography to give 7-chloro-2-{2-[1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazol-3-yl]-ethyl}-quinoxaline (17 mg, 51.1%) as light red oil. MS: m/z=449.4 (M+H+)

Workup

  1. customfor 2.5 h
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-0068f9af486f47e8b12f773919012463
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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