Cesium carbonate → N-(6-Methoxy-pyridazin-3-yl)-2,2-dimethyl-propionamide

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Reaction Steps

3-Chloro-6-methoxy-pyridazine (10.0 g, 69. 18 mmol) is mixed with 2,2-dimethyl-propionamide (8.40 g, 83.01 mmol), BINAP (2.15 g, 3.46 mmol), Cs2CO3 (33.8 g, 103.8 mmol) in dioxane (150 mL). It is degassed by passing N2 through for 10 min at rt. Pd2(dba)3 (3.16 g, 3.46 mmol) is then added and the resulting reaction is refluxed overnight. The reaction is cooled to rt, diluted with EtOAc (150 mL); filtered through silica gel; washed with EtOAc (2×150 mL). The filtrate is washed with H2O (2×300 mL); dried with MgSO4; filtered and concentrated. Purification of the crude material by chromatography gives the title compound (6.59 g, 31.53 mmol, 46%). 1H NMR (CDCl3): δ. 1.35 (s, 9H), 4.08 (s, 3H), 7.01 (d, J=9.7 Hz, 1H), 8.41 (d, J=9.7 Hz, 1H), 8.44 (bs, 1H) ppm. ES-MS (m/z): calcd for C10H15N3O2 (M+H)+: 210.3. found: 210.1.

Provenance & Evidence