Sodium Hydroxide → 3-(2-(2,4-Difluorophenoxy)pyrido[3,2-d]pyridazin-5-yl)-4-methylbenzamide

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Reaction Steps

A mixture of 5-chloro-2-(2,4-difluorophenoxy)pyrido[3,2-d]pyridazine (Example 3, step 5; 130 mg, 0.44 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (144 mg, 0.55 mmol), sodium carbonate hydrate (220 mg, 1.77 mmol), and PdCl2(PPh3)2 (16 mg, 22 μmol) in DME:EtOH:H2O=7:2:3 (2.5 mL) was heated at 130° C. for 30 min in a microwave. The reaction mixture was treated with 5 mL of 1 N NaOH and extracted with EtOAc (2×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. Purification on the ISCO (12 g column, eluted with 40-100% EtOAc in hexanes) afforded the title compound as a tan amorphous solid. MS (ESI, pos.ion) m/z: M+1=393.0

Provenance & Evidence