Potassium Carbonate → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-pyridin-3-ylthiophene-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-pyridin-3-ylthiophene-3-carbonitrile (76 mg, 0.38 mmol), 4-[(6-bromopyridin-2-yl)methyl]morpholine (Example 45, Step 1) (97 mg, 0.38 mmol), dibenyzlideneacetone bis(triphenylphosphine) (17.29 mg, 0.02 mmol), 2-dicylohexylphosphino-2′,4′,6′-triisopropyl-1,1-biphenyl (45.0 mg, 0.09 mmol), and potassium carbonate (57.4 mg, 0.42 mmol) were dissolved in tert-amyl alcohol (3.8 ml) and the mixture was bubbled with nitrogen for 5 min. The reaction was then heated to 100° C. overnight. The mixture was diluted with ethyl acetate and water and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol to afford the title compound as a solid.

Provenance & Evidence