Potassium Phosphate, Tribasic → HCID 71534335, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (611 mg, 2 mmol), ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (828 mg, 3.00 mmol), potassium phosphate (1.06 g, 5.00 mmol) and X-phos (381 mg, 800 μmol) were combined with dioxane (29.4 ml) and water (2.94 ml) to give a light yellow suspension. The mixture was evacuated and back-filled with argon three times, then Pd2(dba)3 (183 mg, 200 μmol) was added and the mixture heated to 125° C. in a microwave for 60 min. The mixture was filtered and the filtrate concentrated. The residue was purified by chromatography (silica, 160 g, 20% to 50% EtOAc in hexanes, gradient over 20 min) to give ethyl 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (284 mg, 677 μmol, 34%) as an off-white powder. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 8.55-8.68 (m, 2H) 8.20 (dd, J=13.79, 7.74 Hz, 2H) 7.96 (d, J=1.51 Hz, 1H) 7.52-7.71 (m, 2H) 7.19 (d, J=8.31 Hz, 1H) 6.73 (d, J=8.31 Hz, 1H) 4.45 (q, J=7.18 Hz, 2H) 4.20 (s, 3H) 3.82-3.97 (m, 3H) 1.44 (t, J=7.18 Hz, 3H); LC/MS: 420.2 [MH]+.

Provenance & Evidence