Lithium hydroxide, monohydrate → 5-Cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid

HRID 1011968Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:8][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)[C:10]=1[CH:11]1[CH2:13][CH2:12]1)=[O:5])C.O.[OH-].[Li+]>C1COCC1.CO.O.C(Cl)Cl>[CH:11]1([C:10]2[N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:22])[F:23])[CH:15]=3)[N:8]=[C:7]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[C:6]=2[C:4]([OH:5])=[O:3])[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (154 mg, 0.37 mmol) in 2 ml THF, 1 ml methanol and 1 ml water, was added lithium hydroxide monohydrate (26 mg, 1.11 mmol). The solution was heated at 80° C. for 2 h. The reaction mixture was cooled, diluted with CH2Cl2 and washed with water. The aqueous phases were extracted with three portions of CH2Cl2. The combined organic layers were dried over magnesium sulfate, and evaporated to deliver a white solid (128 mg, 89%) of the tide compound. MS: 388.2 (M−H−).

Workup

temperatureThe reaction mixture was cooled
washwashed with water
extractionThe aqueous phases were extracted with three portions of CH2Cl2
dry with materialThe combined organic layers were dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-57c0dea084844985979a8830900e4ce2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977358B2

Reaction notes

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