Cesium carbonate → HCID 86682713, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-(8-bromoimidazo[1,2-b]pyridazin-6-yl)benzoate (250 mg, 0.75 mmol), 6-(3-aza-bicyclo[3.1.0]hexan-3-yl)pyridin-2-amine (198 mg, 1.13 mmol), Pd2(dba)3 (43 mg, 0.075 mmol), BINAP (187 mg, 0.3 mmol), Cs2CO3 (734 mg, 2.25 mmol) and dioxane (10 mL) was heated to 100° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give crude product which was further purified by prep-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; gradient conditions: 30% acetonitrile/70% water (0.1% TFA, v/v) initially, proceeding to 50% acetonitrile/50% water (0.1% TFA, v/v) in a linear fashion over 9 min) to give methyl 3-(8-(6-(3-aza-bicyclo[3.1.0]hexan-3-yl)pyridine-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (70 mg, 22%) as a light yellow solid. [M+H]+, 427.1, tR=1.926 min.

Provenance & Evidence