HCID 22172777, compound → Ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate

HRID 1437830Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:8]2[C:12](O)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][C:10]([C:19]([F:22])([F:21])[F:20])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]([C:19]([F:22])([F:20])[F:21])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Sulfuric acid (concentrated, 2 drops) was added to ethyl 1-(3-chloro-2-pyridinyl)-4,5-dihydro-5-hydroxy-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (i.e. the product of Example 3) (1 g, 2.96 mmol) in acetic acid (10 mL) and the mixture was warmed to 65° C. for about 1 hour. The mixture was allowed to cool to 25° C. and most of the acetic acid was removed under reduced pressure. The mixture was partitioned between saturated aqueous sodium carbonate solution (100 mL) and ethyl acetate (100 mL). The aqueous layer was further extracted with ethyl acetate (100 mL). The combined organic extracts were dried and evaporated to give the product as an oil (0.66 g, 77% yield).

Workup

customwas removed under reduced pressure
customThe mixture was partitioned between saturated aqueous sodium carbonate solution (100 mL) and ethyl acetate (100 mL)
extractionThe aqueous layer was further extracted with ethyl acetate (100 mL)
customThe combined organic extracts were dried
customevaporated

Sources & evidence

ORD record: ord-91549444b511487b862df3d5f41d58e4
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622595B2

Reaction notes

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