Sodium Bicarbonate → HCID 90408880, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (7.50 g, 17.33 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (6.43 g, 20.80 mmol), tetrakis(triphenylphospine)palladium (0.801 g, 0.693 mmol) and aqueous sodium bicarbonate (40 mL) in N,N-dimethylformamide (160 mL) was flushed with nitrogen and heated at 85° C. for 24 hours. The mixture was diluted with water and brine and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography on silica (ISCO Companion), eluting with a gradient of 8:2 to 7:3 heptanes/ethyl acetate to give the title compound. MS (ESI+) m/z 488.0 (M+H)+.

Provenance & Evidence