Cesium carbonate → HCID 66742595, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-6-chloro-2-methylpyridazin-3(2H)-one (2.18 g, 9.75 mmol, Eq: 1.30), 5-(1-(azetidin-1-yl)-2-methylpropan-2-yloxy)pyridin-2-amine (1.66 g, 7.5 mmol, Eq: 1.00), Xantphos (651 mg, 1.13 mmol, 0.15 equiv) and Cs2CO3 (8.55 g, 26.3 mmol, 3.5 equiv) were combined in dioxane and the reaction mixture was degassed under vacuum with argon displacement. To the solution was added the Pd2(dba)3 (515 mg, 563 μM, 0.075 equiv) and the mixture was degassed again with argon. The reaction mixture was stirred under argon at 90° C. for 18 hrs before cooling to ambient temperature. The reaction mixture was filtered through a plug of celite. The celite cake was washed with THF and dichloromethane. The combined filtrate and washes were concentrated in vacuo. The crude product was purified by Analogix MPLC (60 g column; elute with 0.5% to 15% MeOH/DCM) to afford the desired product (1.43 g) as a tan solid. (M+H)+=364 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.24 (s, 6 H) 2.12 (quin, J=7.08 Hz, 2 H) 2.59 (s, 2 H) 3.35 (t, J=6.99 Hz, 4 H) 3.81 (s, 3 H) 6.83 (d, J=8.69 Hz, 1 H) 7.32 (dd, J=8.88, 2.83 Hz, 1 H) 8.09 (d, J=3.02 Hz, 1 H) 8.18 (s, 1 H) 8.25 (s, 1 H).

Provenance & Evidence