1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde → 2-Methyl-3-[2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-quinoxaline

HRID 1054941Notes

Reaction equation

HRID 1054941 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[Cl-].[CH3:15][C:16]1[C:17]([CH2:26][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:18][C:19]2[C:24]([N:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>>[CH3:15][C:16]1[C:17]([CH:26]=[CH:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[N:5]=2)=[N:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:25]=1

Participants

3

Reactant 2

HCID 838754401-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehydeHCID 90016889((3-Methylquinoxalin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 1238137142-Methyl-3-[2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-quinoxalineYield 56.3%

Procedure

Was prepared in the same manner as described in General Procedure Example 1g) using 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (50 mg, 277 μmol, Eq: 1.00) and ((3-methylquinoxalin-2-yl)methyl)triphenylphosphonium chloride (126 mg, 277 μmol, Eq: 1.00) as starting materials. Chromatography afforded 2-Methyl-3-[2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-quinoxaline (50 mg, 56.2%) as light yellow solid. MS: m/z=321.4 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-9dd7a55a57b14ad7bf54176318b888bd
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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