Cesium carbonate → HCID 86689711, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with methyl 4,6-dichloropyridazine-3-carboxylate (200 mg, 0.966 mmol), 5-(methylsulfonyl)pyridin-2-amine (183 mg, 1.06 mmol), Pd2(dba)3 (88.5 mg, 0.097 mmol), xantphos (112 mg, 0.193 mmol) and cesium carbonate (944 mg, 2.9 mmol). 1,4-Dioxane (6.0 mL) was added and argon was bubbled through it while sonicating the flask for 5 min. The flask was sealed and heated at 100° C. for 1 h. After cooling the mixture was filtered through celite and the filter cake washed with CH2Cl2. The filtrates were concentrated in vacuo then purified by chromatography (spherical silica 20-45 μM, 23 g, Versaflash Supelco, 0 to 100% ethyl acetate in hexanes, 30 min) to give methyl 6-chloro-4-(5-(methylsulfonyl)pyridin-2-ylamino)pyridazine-3-carboxylate (62 mg, 19%) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.18 (s, 1H) 9.31 (s, 1H) 8.98 (d, J=2.27 Hz, 1H) 8.19 (dd, J=8.59, 2.53 Hz, 1H) 7.09 (dd, J=8.84, 0.76 Hz, 1H) 4.15 (s, 3H) 3.15 (s, 3H). LCMS (EI/CI) m/z: 342.9 [M+H].

Provenance & Evidence