Potassium Carbonate → Ethyl 1-(3-Chloro-2-pyridyl)-4-formyl-pyrazole-3-carboxylate

HRID 1517603Notes

Reaction equation

[CH:1]([C:3]1[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5][NH:6][CH:7]=1)=[O:2].[Cl:13][C:14]1[C:15](F)=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:13][C:14]1[C:15]([N:6]2[CH:7]=[C:3]([CH:1]=[O:2])[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5]2)=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 4-formyl-pyrazole-3-carboxylate (1.70 g, 10.1 mmol) and 3-chloro-2-fluoropyridine (1.99 g, 15.1 mmol) in dimethylformamide (20 mL) is added potassium carbonate (2.80 g, 20.2 mmol) and the mixture is stirred at 100° C. for 16 hours. After completion, the reaction mixture is partitioned between water (25 mL) and ethyl acetate (25 mL). The aqueous layer is extracted with ethyl acetate (3×25 mL) and the combined organic extracts are dried over sodium sulfate, concentrated in vacuo and purified by column chromatography over silica gel eluting with hexane/ethyl acetate (50:50) to yield 1.5 g (54%) of the title compound. MS (m/z): 280 (M+1).

Workup

customAfter completion, the reaction mixture is partitioned between water (25 mL) and ethyl acetate (25 mL)
extractionThe aqueous layer is extracted with ethyl acetate (3×25 mL)
dry with materialthe combined organic extracts are dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by column chromatography over silica gel eluting with hexane/ethyl acetate (50:50)

Sources & evidence

ORD record: ord-a01e42f889b9438198403bf55ad908e8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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