Cesium carbonate → 6-chloro-2-methyl-4-(5-((1R,5S)-3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (492 mg, 2.20 mmol), 5-(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-amine (437 mg, 2.0 mmol), Xantphos (86.8 mg, 150 μmol) and cesium carbonate (1.95 g, 6.00 mmol) in dry dioxane (10 ml) was vacuum de-gassed and place under argon atmosphere. To this mixture was added tris(dibenzylideneacetone)dipalladium (0) (31.1 mg, 30 μmol) and the vacuum de-gas cycle was repeated. The reaction was heated at 90° C. (oil bath) with vigorous stirring overnight. The flask was cooled to ambient and the contents were filtered through a plug of celite, rinsing well with dioxane. The combined filtrate and washes were concentrated. The resultant crude residue was triturated with ether to provide the desired product as a light yellow solid (345 mg, 47.8%).

Provenance & Evidence