Cyclopentylamine → Ethyl 4-cyano-3-(cyclopentylamino)benzoate

Temperatur

100 °C

A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), XANTPHOS (228 mg, 0.39 mmol), cesium carbonate (1.282 g, 3.94 mmol), cyclopentylamine (233 mg, 2.75 mmol), and tris(dibenzylideneacetone)dipalladium (180 mg, 0.20 mmol) in dioxane (5 mL) was stirred at 100° C. for 17 h. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL), the organic layer washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes:ethyl acetate 9:1) afforded ethyl 4-cyano-3-(cyclopentylamino)benzoate (366 mg, 72% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): 7.43 (m, 2H), 7.35 (m, 1H), 7.27 (m, 1H), 4.62 (d, 1H), 4.38 (q, 2H), 3.93 (m, 1H), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.53 (m, 2H), 1.39 (t, 3H). MS (EI) for C15H18N2O2: 259 (MH+).

1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL)
2. washthe organic layer washed with brine (50 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated

ORD-Eintrag

ord-b3eb8b5c8fab49148cfdb80524cfa6a5

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08012956B2