Cesium carbonate → 3-Chloro-N-[6-methyl-3-[3-(methyloxy)phenyl]-2-(1-pyrrolidinyl)thieno[2,3-b]pyridin-4-yl]-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (50 mg, 0.095 mmol) (Example 33), pyrrolidine (0.039 mL, 0.477 mmol), Pd2(dba)3 (8.74 mg, 9.54 μmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (8.11 mg, 0.019 mmol) and Cs2CO3 (93 mg, 0.286 mmol) in THF (1 mL) was heated at 70° C. for 19 h. The mixture was then filtered through celite and the filtrate concentrated. Purification by chromatography on silica gel, eluting with a gradient of 20-50% ethyl acetate in DCM was followed by further purification by MDAP (acidic conditions), to give the title compound (3.9 mg). LCMS (A) m/z: 514 [M+1]+, Rt 1.56 min (acidic), Rt 1.09 min (basic).

Provenance & Evidence