Cesium carbonate → HCID 66801413, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-bromo-7-fluorothiazolo[5,4-c]pyridin-2-yl)-3-chlorobenzonitrile (0.110 g, 0.30 mmol), 6-methylpyrimidin-4-ylamine (35 mg, 0.32 mmol), XantPhos (0.018 g, 0.03 mmol) and Cs2CO3 (247 mg, 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 at 80° C. for 2 hours in a sealed vial. After cooling to room temperature, the crude reaction mixture was filtered through Celite® washing with EtOAc (50 mL). The filtrate was concentrated to dryness under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-100% EtOAc in DCM, then triturated with diethyl ether (×2), to afford the title compound as a pale yellow solid (43 mg, 36% yield). 1H NMR (400 MHz, CDCl3): δ 8.73 (d, J=1.2 Hz, 1H), 8.34 (d, J=1.8 Hz, 1H), 7.86-7.76 (m, 3H), 7.66 (t, J=8.0 Hz, 1H), 7.57 (br s, 1H), 2.56 (s, 3H). LCMS (Method C): RT=3.31 min, m/z: 397 [M+H+].

Provenance & Evidence