Cesium carbonate → HCID 24801837, compound

Participants

Reaction Steps

A mixture of 4-benzylpyrrolidin-2-one (0.068 g, 0.39 mmol), N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (0.10 g, 0.32 mmol), cesium carbonate (0.16 g, 0.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.006 g, 0.060 mmol) and xantphos (0.008 g, 0.013 mmol) in anhydrous toluene (3 mL) was subjected to microwave irradiation at 120° C. for 15 min. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexanes (1/1)) to afford the title compound as a white solid (0.017 g, 13%): mp 143-144° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.38-7.11 (m, 10H), 5.91 (br s, 1H), 4.56 (d, J=5.5 Hz, 2H), 4.25-4.13 (m, 1H), 3.85-3.72 (m, 1H), 2.95-2.68 (m, 4H), 2.61 (s, 3H), 2.52-2.39 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 173.0, 162.3, 155.3, 152.6, 138.2, 137.9, 128.8, 128.7, 127.9, 127.6, 126.8, 118.6, 52.6, 44.0, 40.1, 37.7, 33.4, 17.2; MS (ES+) m/z 406.3 (M+1).

Provenance & Evidence