Water → ethyl 1-[(4-bromo-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257341Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([CH2:7]Cl)[S:5][CH:6]=1.[NH:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([CH2:7][N:9]2[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]2)[S:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution (4 mL) of the compound (1.57 g, 7.39 mmol) obtained in Example 30b in N,N-dimethylformamide were added ethyl 1H-pyrazole-4-carboxylate (1.3 g, 9.28 mmol) and potassium carbonate (1.5 g, 10.9 mmol), and the mixture was stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (1.51 g, 66%) as a pale-brown oil.

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained crude product
customwas purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record: ord-8fb6c95600394397a71530674883142d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461348B2

Reaction notes

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