Dimethylformamide → 1-(3-Chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde

HRID 1517597Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].FN1C=C[CH:19]=[CH:18][CH:17]1[Cl:22].[CH3:23][N:24]([CH3:27])C=O>O>[Cl:22][C:17]1[C:23]([N:4]2[CH:5]=[C:6]([CH:7]=[O:8])[C:2]([CH3:1])=[N:3]2)=[N:24][CH:27]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 3-methyl-pyrazole-4-carbaldehyde (0.5 g, 4.5 mmol) in dry dimethylformamide (15 mL) is added potassium carbonate (2.5 g, 18 mmol,) at room temperature. The reaction mixture is stirred at 40° C. for 30 min and then 1-fluoro-2-chloropyridine (0.77 g, 6 mmol,) is added. The reaction mixture is heated at 70° C. for 16 h. After completion, the reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture is purified by chromatography on silica gel eluting with hexane/ethyl acetate (75:25, 65:35) to yield 0.525 g (52%) of the title compound. MS (m/z): 222 (M+1).

Workup

temperatureThe reaction mixture is heated at 70° C. for 16 h
temperatureAfter completion, the reaction mixture is cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude mixture is purified by chromatography on silica gel eluting with hexane/ethyl acetate (75:25, 65:35)

Sources & evidence

ORD record: ord-b20cf038e506491fad97d4ca41cc6b6b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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