Potassium Phosphate, Tribasic → 4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-N-(2-dimethylaminoethyl)benzamide

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Reaction Conditions

Reaction Steps

The following conditions were used. Tris(dibenzilideneacetone)dipalladium (47.2 mg), tricyclohexylphosphine (28.9 mg) and potassium phosphate (656 mg) were added to a degassed solution of 5-bromo-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (300 mg, 1.03 mmol), N-(2-dimethylaminoethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (361 mg, 1.13 mmol) in 1,4-dioxane (2 ml) and water (0.400 ml) under nitrogen atmosphere. The suspension was stirred at 90° C. for 4 hours. The mixture was filtered and the solvent was removed. The mixture was adsorbed on silica gel, the crude product was purified by flash chromatography on silica gel eluting with 10% methanol in dichloromethane follow by 10% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-N-(2-dimethylaminoethyl)benzamide after stirring overnight in acetonitrile. NMR Spectrum: (DMSO-d6) 2.19 (s, 6H), 2.42 (t, 2H), 3.35-3.42 (m, 2H), 7.50 (dd, 1H), 7.84 (d, 2H), 7.91 (bs, 2H), 7.95 (d, 2H), 8.26 (dd, 1H), 8.45 (t, 1H), 8.56 (dd, 1H), 8.61 (d, 1H), 8.73 (d, 1H); Mass spectrum: M+H+ 403

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