Water → ethyl 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoate

To a solution of ethyl 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate (50 mg, 0.13 mmol) in DMF (2.0 mL) was added sodium hydride (60 wt % oil 6.19 mg, 0.15 mmol) at 0° C., and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added benzyl bromide (0.018 mL, 0.15 mmol) at 0° C., and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane) to give ethyl 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoate (15.9 mg, 0.033 mmol, 25.8%) as a colorless oil.

1. stirringthe mixture was stirred at room temperature for 4 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. customdried
5. customthe solvent was evaporated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane)

ORD-Eintrag

ord-e57632c1e23c4dc98ab84282cebea13e

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09156837B2