Hydrochloric Acid → HCID 89495427, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,5-dibromopyridine (378 mg, 1.6 mmol), 3-hydroxy-N-(2,2,2-trifluoroethyl)-D-valinamide.HCl I-27b (400 mg, 1.6 mmol), potassium carbonate (882 mg, 6.38 mmol) and L-proline (36.7 mg, 0.319 mmol), in DMSO (5 mL) and degassed with nitrogen was added copper(I) iodide (STREM crushed) (30.4 mg, 0.160 mmol). The reaction was sealed and heated at 80° C. for 64 h. The reaction was quenched into water and extracted with DCM. The organic layer was washed with aq. NaHCO3, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (EtOAc/hexane; 25-100%) to afford the title compound I-27. MS APCI: [M+H]+ m/z=371.1. 1H NMR (600 MHz, DMSO) δ 8.57 (t, J=6.5 Hz, 1H), 8.03 (s, 1H), 7.78 (s, 1H), 7.17 (s, 1H), 6.17 (d, J=6.5 Hz, 1H), 4.77 (s, 1H), 3.85 (m, 2H), 3.80 (d, J=6.5 Hz, 1H), 1.07 (s, 3H), 1.06 (s, 3H).

Provenance & Evidence