Dichloromethane → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (85 mg, 0.403 mmol) in dioxane (4 mL) was added bis(pinacolato)diboron (123 mg, 0.483 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (33 mg, 0.040 mmol), potassium acetate (120 mg, 1.21 mmol). The mixture was degassed and heated at 100° C. for 2 h. The mixture was cooled, and then added (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (100 mg, 0.201 mmol), tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.02 mmol), K2CO3 (139 mg, 1.00 mmol) and water (1.3 mL, degassed). The reaction mixture was heated at 100° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4 and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C30H30ClN3O3S: 548.3 (M+H+); Found: 548.3 (M+H+).

Provenance & Evidence