Cesium carbonate → HCID 58007509, Verbindung

To a solution of N-(2,5-dimethyl-2H-pyrazol-3-yl)-2-oxo-2-phenyl-acetamide (200 mg, 0.82 mmol) in DMF (2 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in THF, 1.1 mL, 0.99 mmol) over a period of 5 min. The ice bath was removed and the solution was stirred for 1 h at ambient temperature. After the addition of 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (which might be prepared according to WO2005123748, 250 mg, 0.99 mmol) the reaction mixture was stirred for 18 h at ambient temperature. After the addition of cesium carbonate (1.40 g, 4.11 mmol) and further 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (996 mg, 3.95 mmol) it was stirred for 20 h at ambient temperature. The resulting mixture was diluted with TBME (15 mL) and washed twice with water (10 mL) and brine (10 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (113 mg, 33%) as a light brown oil. MS m/e: 416.3 [M+H]+.

1. customThe ice bath was removed
2. stirringwas stirred for 18 h at ambient temperature
3. stirringwas stirred for 20 h at ambient temperature
4. washwashed twice with water (10 mL) and brine (10 mL)
5. extractionThe combined aqueous layers were extracted with TBME (15 mL)
6. dry with materialthe combined organic layers were dried over sodium sulfate
7. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

ORD-Eintrag

ord-c8f476fd74ca4195af549c10a2335ded

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08133909B2