Cesium carbonate → HCID 66801834, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine (0.113 g, 0.30 mmol), 6-methylpyrimidin-4-ylamine (0.036 g, 0.33 mmol), XantPhos (0.018 g, 0.030 mmol) and Cs2CO3 (0.247 g, 0.75 mmol) in dioxane (2.5 mL) was degassed with a stream of argon. Pd2(dba)3 (0.014 g, 0.015 mmol) was added and the reaction mixture was heated in a sealed vial at 80° C. for 3 hours. After cooling to room temperature, the crude reaction 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 (71 mg, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.68 (s, 1H), 8.61 (d, J=1.1 Hz, 1H), 8.49 (d, J=1.9 Hz, 1H), 7.77-7.72 (m, 2H), 7.71-7.66 (m, 1H), 7.42 (s, 1H), 2.38 (s, 3H). LCMS (Method C): RT=3.73 min, m/z: 406 [M+H+].

Provenance & Evidence