Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoate → ethyl 1-(6-methyl-3-pyridyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylate

HRID 1437271Notes

Reaction equation

HRID 1437271 reaction equation
[NH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)[NH2:2].[CH2:10]([O:12][C:13](=[O:25])[C:14](=O)[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=O)[CH3:11]>>[CH2:10]([O:12][C:13]([C:14]1[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:1]([C:3]2[CH:8]=[N:7][C:6]([CH3:9])=[CH:5][CH:4]=2)[N:2]=1)=[O:25])[CH3:11]

Participants

3

Reactant 2

HCID 12171345Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoateHCID 221471375-Hydrazinyl-2-methylpyridine

Product 1

HCID 23143706ethyl 1-(6-methyl-3-pyridyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylate

Procedure

The general procedure of Referential Example 3-2) was repeated through use of the 5-hydrazino-2-methylpyridine (1.20 g) prepared in Referential Example 63 and the 4-(2-pyridyl)-2,4-dioxobutanoic acid ethyl ester (3.48 g) prepared in Referential Example 31, to thereby give the title compound as an oily product (0.459 g, 15%).

Workup

  1. customprepared in Referential Example 63

Sources & evidence

ORD record
ord-b8ba178f31b04c958f82eef853e3dad0
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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