HCID 131736341, compound → HCID 72704704, compound

HRID 1054969Notes

Reaction equation

HRID 1054969 reaction equation
[CH2:1]([N:3]1[C:7]([CH:8]=[CH:9][C:10]2[C:19]([CH3:20])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[N:6][C:5]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[N:4]1)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][C:10]2[C:19]([CH3:20])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[N:6][C:5]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 131736341HCID 131736341, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72704704HCID 72704704, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-(1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-3-methylquinoxaline (10 mg, 29.9 μmol, Eq: 1.00) was stirred in Ethyl acetate (6 ml) using 5% Pd on Ba2SO4 (3 mg, 30.8 μmol, Eq: 1.00) as catalyst in a hydrogen atmosphere. The mixture was stirred at room temperature for totally 12 h. TLC showed nearly complete conversion. The crude material was applied on silica gel an purified by column chromatography using ethyl acetate/methanol (0-5% methanol) as eluent to give 2-[2-(2-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-3-methyl-quinoxaline (3.2 mg, 31.8%) as off-white semisolid

Workup

  1. customan purified by column chromatography

Sources & evidence

ORD record
ord-e40dd04c57f24bf9a178125eacf09c78
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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