Potassium Hydroxide → 2-(5-(5-hydroxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

Participants

Reaction Conditions

Reaction Steps

To a nitrogen gas purged microwave vial of 2-(5-(5-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide 2-1a (800 mg, 1.439 mmol), 2-DI-T-BUTYLPHOSPHINO-3,4,5,6-TETRAMETHYL-2′,4′,6′-TRI-I-PROPYLBIPHENYL (55.3 mg, 0.115 mmol) and Pd2 dba3 (26.3 mg, 0.029 mmol) in Dioxane (6 ml) was added 1 M KOH (4.32 ml, 4.32 mmol). The reaction mixture was sealed and heated in an oil bath at 100° C. for 18 h. The reaction was cooled, diluted with brine and product extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered and concentrated to an oil. The oil was diluted with diethyl ether (18 ml) and sonicated. The resulting solid was filtered and washed with ether to give 720 mg white solid, 2-1b.

Provenance & Evidence