2-Bromopyridine → HCID 89630048, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-N-[3-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]phenyl]prop-2-enamide (200 mg, 0.370 mmol) in N,N-dimethylformamide (3.0 mL) under nitrogen, was added Pd(dppf)Cl2CH2Cl2 (16 mg, 0.020 mmol), 2-bromopyridine (60 mg, 0.38 mmol), and a solution of sodium carbonate (120 mg, 1.13 mmol in water, 1 mL). The resulting solution was stirred for 2 hours at 80° C. before being cooled and extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-100% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford N-(3-(5-(pyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a yellow oil. LRMS (ESI) calc'd for C27H32N5O2Si [M+H]+: 486, found 486.

Provenance & Evidence