Cesium fluoride → (R)-3-methyl-2-(5-(5-((2-(pyrrolidin-1-yl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-N-(2,2,2-trifluoroethyl)butanamide

Participants

Reaction Conditions

Reaction Steps

In a microwave vial containing (R)-3-methyl-2-(5-(5-((2-(pyrrolidin-1-yl)ethoxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-N-(2,2,2-trifluoroethyl)butanamide 9-1a (60.7 mg, 0.094 mmol), added DMSO (1 ml, 0.094M) followed by Cesium Fluoride (284 mg, 1.871 mmol). The reaction mixture was heated at 140° C. for one hour on an oil bath open to air. LC/MS indicated conversion to product, the reaction mixture was filtered through a fine filter funnel and purified on the Gilson HPLC instrument using acetonitrile: water with 0.1% TFA buffer system using 10-60% gradient to give the title compound 9-1 (3.32 mg, 5.61%). LRMS (ESI) m/z 519.3 [(M+H)+; calcd for C26H33F3N6O2: 519.3]

Provenance & Evidence