Dimethylformamide → HCID 56654397, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-(2-bromo-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidin-1-yl)(cyclopropyl)methanone (Example 83, 35 mg, 0.06 mmol) in DMF was added ZnCN (15 mg, 0.12 mmol) and the reaction was degassed with N2 purge. Pd(PPh3)4 (4 mg, 0.003 mmol) was added and the reaction mixture was heated under microwave irradiation at 150° C. for 15 minutes. Next, the reaction mixture was diluted with water and extracted with EtOAc (75 mL). The organic phase was dried (Na2SO4) and concentrated under vacuum. Crude product was chromatographed (12 g Redi-Sep column) eluting from 100% heptane to 60:40 EtOAc:heptane to afford the final product (18 mg, 56%) as a solid. 1H NMR (CDCl3) δ ppm: 8.08 (1H), 8.00 (1H), 7.70 (1H), 7.66 (2H), 4.98-4.52 (4H), 4.12 (1H), 3.73 (1H), 1.49 (1H), 1.10-0.81 (4H); m/z (Cl) 560 ([M+H]+.

Provenance & Evidence