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

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-1,3-dimethyl-1H-pyrrolo[2,3-b]pyridine (30 mg, 0.133 mmol) in dioxane (1.4 mL) was added bis(pinacolato)diboron (41 mg, 0.16 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (11 mg, 0.013 mmol), potassium acetate (39 mg, 0.4 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 (33 mg, 0.07 mmol), tetrakis(triphenylphosphine)palladium(0) (8 mg, 0.007 mmol), K2CO3 (48 mg, 0.35 mmol) and water (0.5 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 C31H32ClN3O3S: 562.3 (M+H+); Found: 562.3 (M+H+).

Provenance & Evidence