Potassium Hydroxide → 4-(1-methyl-1H-pyrazol-5-yl)-5-(trifluoromethyl)-2-thiophenecarboxylic Acid

HRID 1845657Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:16]([O:18]C)=[O:17])[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=[N:3]1.[OH-].[K+]>C1COCC1.O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:16]([OH:18])=[O:17])[S:10][C:11]=2[C:12]([F:13])([F:14])[F:15])=[CH:5][CH:4]=[N:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(1-methyl-1H-pyrazol-5-yl)-5-(trifluoromethyl)-2-thiophenecarboxylate (250 mg, 0.77 mmol), in THF/H2O (3 mL/0.3 mL), was added KOH (217 mg, 3.88 mmol). The reaction mixture was heated to 50° C. for 4 h. After the mixture was concentrated and diluted with H2O, the pH was adjusted to 3. The mixture was extracted with DCM (5 mL×3). The collected organic layers were concentrated under vacuum to give crude acid (235 mg, 80% pure) which was used directly in the next step without further purification: LC-MS (ES) 277 (M+H)+.

Workup

concentrationAfter the mixture was concentrated
additiondiluted with H2O
extractionThe mixture was extracted with DCM (5 mL×3)
concentrationThe collected organic layers were concentrated under vacuum

Sources & evidence

ORD record: ord-3c838d7c265b402e86b709bf497df339
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946278B2

Reaction notes

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