Cesium fluoride → HCID 66762983, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-6-(3-chloro-5-methylphenyl)-N-(3,4-dimethoxybenzyl)pyridazine-4-carboxamide (3-1, 0.01 g, 0.023 mmol, 1.0 equiv; made analogously to 1-3) in DMF (0.50 mL) at 25° C. was added 2-tributylstannylpyridine (0.017 g, 0.046 mmol, 2.0 equiv), cesium fluoride (0.007 g, 0.046 mmol, 2.0 equiv), copper (I) iodide (0.00044 g, 0.0023 mmol, 0.1 equiv), and tetrakis(triphenylphosphine) palladium(0) (0.0027 g, 0.0023 mmol, 0.1 equiv) and the reaction mixture was heated to 80° C. for 0.5 hours. The reaction was cooled and partitioned between EtOAc and water. The organic phase was dried over MgSO4 and concentrated. The reaction mixture was purified by normal phase column chromatography (0 to 100% EtOAc in hexanes) to give the product (3-2) as a tan solid. HRMS [M+H] C25H27ClN4O4 calc'd 475.1531. found 475.1549.

Provenance & Evidence