Ethanolamine → 2-[4-(5-Trifluoromethyl-1H-pyrazol-3-yl)-phenoxy]-ethylamine

HRID 413307Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].CC(C)([O-])C.[K+].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:22][N:21]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:19]=2)=[CH:14][CH:13]=1.O>CS(C)=O>[F:26][C:23]([F:24])([F:25])[C:20]1[NH:21][N:22]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:2][CH2:1][CH2:3][NH2:4])=[CH:13][CH:14]=2)[CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

In a flame-dried, round-bottomed flask, ethanolamine (836 mg, 13.7 mmol) was dissolved in dimethylsulfoxide (2.7 ml), and potassium tert-butoxide (95%, 1.54 g, 13.7 mmol) was added to the solution. This mixture was stirred at about 65° C. for about ten minutes, and then 5-(4-fluoro-phenyl)-3-trifluoromethyl-1H-pyrazole (630 mg, 2.74 mmol) was added. The dark-colored solution was heated to about 85° C. for about eighteen hours, and was then allowed to cool to room temperature. Water was added, and the resulting tan-colored solid was collected by filtration. This crude product was purified by column chromatography (5% methanol/dichloromethane to 20% methanol/dichloromethane) to afford the product as a white solid (255 mg, 25% yield). LRMS ([M+H]+)=272.2.

Workup

temperatureThe dark-colored solution was heated to about 85° C. for about eighteen hours
temperatureto cool to room temperature
filtrationthe resulting tan-colored solid was collected by filtration
customThis crude product was purified by column chromatography (5% methanol/dichloromethane to 20% methanol/dichloromethane)

Sources & evidence

ORD record: ord-44a52068054f4ffebf2b622f6635d783
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566377B2

Reaction notes

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