Sodium Carbonate → 4-bromo-1-isopropyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-bromo-3-iodo-1-isopropyl-1H-pyrrolo[2,3-b]pyridine (D10) (2.80 g, 7.67 mmol), (3-(pyrrolidin-1-yl)phenyl)boronic acid (1.612 g, 8.44 mmol), bis(triphenylphosphine)palladium(II) chloride (0.538 g, 0.767 mmol) and 2M sodium carbonate aqueous solution (9.59 mL, 19.18 mmol) in ACN (35.0 mL) was heated at 65° C. for 2 hours and then allowed to cool to RT. The mixture was evaporated to dryness and the residue partitioned between water (50 mL) and ethyl acetate (150 mL). The aqueous phase was separated and extracted with additional ethyl acetate (100 mL). The organic extracts were combined, washed with brine (50 mL), dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica eluting with cyclohexane and ethyl acetate (0-35%) to give an impure material which was further purified on silica eluting with cyclohexane and ethyl acetate (0-25%). The appropriate fractions were combined and evaporated to dryness producing the title compound (692 mg). LCMS (A): m/z (M+H)+ 384/386, C20H22BrN3 requires 383/385 (acidic).

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