Cesium carbonate → HCID 56952518, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 4,7-dibromo-2-(2-chloro-6-fluoro-phenyl)thiazolo[5,4-c]pyridine (0.227 mmol; 96 mg), 6-methylpyrimidin-4-amine (0.34 mmol, 37 mg), Pd2(dba)3 (0.011 mmol, 10 mg), XantPhos (0.0227 mmol; 14 mg) and Cs2CO3 (0.4544 mmol, 148 mg) in 1,4-dioxane (3 mL) was heated at 75° C. under nitrogen in an oil bath for 4.5 hours. The reaction mixture was then cooled to room temperature, filtered through celite, washed with EtOAc. The filtrate was concentrated and the resulting crude product was purified by silica gel chromatography (30-100% EtOAc/hexane) to give the title compound as an off-white solid (80 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.76 (s, 1H), 8.64 (s, 1H), 8.59 (s, 1H), 7.77-7.68 (m, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.56-7.48 (m, 2H), 2.39 (s, 3H). LCMS (Method B): RT=4.39 min, m/z 450.0 [M+H+].

Provenance & Evidence