Salicylaldehyde oxime → HCID 42610076, compound

Participants

Reaction Conditions

Reaction Steps

The starting 2-(4-iodophenyl)-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide (130 mg, 0.280 mmol), 3-cyclopropyl-1H-indazole (66.5 mg, 0.420 mmol), copper (I) oxide (2.004 mg, 0.014 mmol), cesium carbonate (146 mg, 0.448 mmol), and salicylaldoxime (7.68 mg, 0.056 mmol) were mixed into 1.0 ml of CH3CN in a sealed bottle. The mixture was stirred at 150° C. overnight. After cooled, water (25 mL) was added and the mixture. Organics were extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient, 30-100% EtOAc in hexanes) to give 2-[4-(3-cyclopropyl-1H-indazole-1-yl)phenyl]-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide as a light yellow solid (94 mg, 68%). 1H NMR (CDCl3, 400 MHz) δ 8.206 (d, J=2.57 Hz, 1H); 7.816 (d, J=8.06 Hz, 1H); 7.683 (m, 3H); 7.407 (m, 3H); 7.208 (m, 3H); 6.726 (d, J=7.14 Hz, 1H); 5.128 (quintet, J=6.96 Hz, 1H); 4.361 (dd, J=15.93, 7.96 Hz, 2H); 3.645 (s, 2H); 2.288 (m, 1H); 1.413 (d, J=6.77 Hz, 3H); 1.175 (m, 2H); 1.085 (m, 2H); MS (ES): m/z 495.2 (M+H). FLIPR alpha1I IP=73 nM.

Provenance & Evidence