Cesium carbonate → HCID 66801709, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-(2-chloro-6-fluorophenyl)-7-fluorothiazolo[5,4-c]pyridine (0.09 g, 0.25 mmol), 6-methylpyrimidin-4-ylamine (0.027 g, 0.25 mmol), XantPhos (0.015 g, 0.025 mmol) and Cs2CO3 (0.206 g, 0.625 mmol) in dioxane (2 mL) was degassed with a stream of argon. Pd2(dba)3 (0.012 g, 0.0125 mmol) was added and the reaction mixture was heated in a sealed vial at 70° C. for 5 hours. After allowing to cool to room temperature, a stream of argon was bubbled through the suspension and additional amounts of Pd2(dba)3 (0.010 g) and XantPhos (0.010 g) were added. The reaction mixture was heated at 80° C. for 18 hours. After cooling to room temperature, the crude mixture was filtered through Celite® washing with EtOAc and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-100% EtOAc in pentane and then triturated with diethyl ether to afford the title compound as an off-white solid (41 mg, 42% yield). 1H NMR (400 MHz, CDCl3): δ 8.71 (s, 1H), 8.30 (d, J=1.9 Hz, 1H), 7.87 (s, 1H), 7.57-7.45 (m, 2H), 7.40 (d, J=8.2 Hz, 1H), 7.21 (t, J=8.7 Hz, 1H), 2.55 (s, 3H). LCMS (Method C): RT=3.54 min, m/z: 390 [M+H+].

Provenance & Evidence