Potassium Phosphate, Tribasic → HCID 46191516, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-N-(3,4-dimethoxybenzyl)-6-(3,5-dimethylphenyl)pyridazine-4-carboxamide (1-3, 0.012 g, 0.029 mmol, 1.0 equiv) in DMF (0.20 mL) was added Pd2(dba)3 (0.0027 g, 0.003 mmol, 0.1 equiv), S-Phos (0.0024 g, 0.006 mmol, 0.2 equiv), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.036 g, 0.18 mmol, 6.0 equiv) and K3PO4 (0.025 g, 0.12 mmol, 4.0 equiv) and the reaction was heated to 175° C. for 30 minutes in the microwave. The reaction mixture was cooled and partitioned between EtOAc and water. The organic phase was washed three times with water and dried over MgSO4 and concentrated. The residue was purified by normal phase column chromatography (5 to 100% EtOAc in hexanes) and then purified by reverse phase column chromatography (5 to 85% ACN in water, 0.1% TFA buffer) to afford the product as a solid after freebasing the purified fractions. HRMS [M+H] C26H27N5O3 calc'd 458.2227. found 458.2210.

Provenance & Evidence