Cesium carbonate → HCID 53373725, compound

Participants

Reaction Steps

To a solution of 2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-4-amine (175 mg, 0.480 mmol), 2-(1-formylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate (194 mg, 0.624 mmol), and Cs2CO3 (267 mg, 0.816 mmol) in DMF (3.0 mL) was heated at 85° C. for 10 h. After cooling to RT, the mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was triturated with EtOAc, filtered, and dried to give the title compound (102 mg, 42%): 1H NMR (DMSO-d6) δ 7.94 (s, 1H), 7.72 (d, J=6.0 Hz, 2H), 7.39 (s, 1H), 6.79 (d, J=6.0 Hz, 2H), 6.66 (s, 1H), 6.41 (s, 2H), 6.07 (s, 2H), 4.20 (t, J=6.8 Hz, 2H), 4.10 (brd, J=13.6 Hz, 1H), 3.62 (brd, J=13.2 Hz, 1H), 2.91 (td, J=12.0, 2.4 Hz, 1H), 2.54 (m, 1H), 1.70 (t, J=6.8 Hz, 2H), 1.57-1.42 (m, 3H), 1.03 (m, 1H), 0.94 (m, 1H); LC/MS [M+H]+ 504.07.

Provenance & Evidence