Dimethylformamide → 6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) (300 mg, 0.890 mmol) and 4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (353 mg, 1.283 mmol) in ACN (2.5 mL) was added 2M sodium carbonate aqueous solution (4.72 mL, 9.43 mmol). DMF (4 mL) and DCM (3 mL) were added to aid the solubility. Then, bis(triphenylphosphine)palladium(II)chloride (81 mg, 0.116 mmol) was added and the reaction was stirred at 55° C. for 30 mins. Volatiles were removed by evaporation before partitioning between DCM and water. The organic layer was separated, dried and concentrated. The crude material was purified on silica eluting with gradient of 0-40% ethyl acetate in cyclohexane to afford the title compound (130 mg). LCMS (A): m/z (M+H)+ 358/360, C17H16BrN3O requires 357/359 (acidic).

Provenance & Evidence