Cesium carbonate → HCID 66802090, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-bromo-7-fluorothiazolo[5,4-c]pyridin-2-yl)-3-chlorobenzonitrile (0.35 g, 0.95 mmol), (6-aminopyrimidin-4-yl)methanol (125 mg, 1.0 mmol), XantPhos (0.055 g, 0.095 mmol) and Cs2CO3 (780 mg, 2.38 mmol) in dioxane (11 mL) was degassed with a stream of argon. Pd2(dba)3 (0.048 g, 0.047 mmol) was added and the reaction mixture was heated at 80° C. for 6 hours in a sealed vial. After cooling to room temperature, the crude reaction mixture was diluted with EtOAc (100 mL) and water (20 mL) and the resultant mixture was filtered through Celite® washing with EtOAc (50 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure The resultant residue was purified by column chromatography on silica gel eluting with 0-10% MeOH in DCM, then triturated with diethyl ether (×2), to afford the title compound as a pale yellow solid (203 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.79 (br s, 1H), 8.61 (d, J=1.2 Hz, 1H), 8.52 (d, J=1.8 Hz, 1H), 8.16-8.08 (m, 2H), 7.86 (t, J=8.0 Hz, 1H), 7.58 (s, 1H), 5.57 (t, J=5.7 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H). LCMS (Method C): RT=3.29 min, m/z: 413 [M+H+].

Provenance & Evidence