Cesium carbonate → HCID 66807262, compound

Participants

Reaction Steps

A mixture of N-[3,5-dichloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-phenyl]-acetamide (0.057 g, 0.15 mmol), 6-methylpyrimidin-4-ylamine (0.020 g, 0.18 mmol), Pd2(dba)3 (0.007 g, 0.0075 mmol), XantPhos (0.017 g, 0.03 mmol) and Cs2CO3 (0.098 g, 0.30 mmol) in dioxane (2 mL) was degassed with a stream of N2 and then subjected to microwave irradiation at 150° C. for 30 minutes. After cooling to room temperature, the crude reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, then dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 50-100% EtOAc in cyclohexane followed by 1% MeOH in EtOAc to afford the title compound as a pale yellow solid (21 mg, 31% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.62 (s, 1H), 10.53 (s, 1H), 8.63 (d, J=1.2 Hz, 1H), 8.44 (d, J=5.6 Hz, 1H), 7.89 (s, 2H), 7.82 (d, J=5.6 Hz, 1H), 7.61 (s, 1H), 2.39 (s, 3H), 2.13 (s, 3H). LCMS (Method C): RT=3.02 min, m/z: 445 [M+H+].

Provenance & Evidence