1-Methylimidazole → 3-Chloro-N-{6-cyano-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-chloro-N-{6-chloro-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 117) (70 mg, 0.146 mmol) in 1-methylimidazole (1 mL) at RT was added potassium ferrocyanide (12.34 mg, 0.029 mmol) and copper(I) iodide (2.78 mg, 0.015 mmol). The reaction mixture was heated to 160° C. under a nitrogen atmosphere. Extra potassium ferrocyanide (12.34 mg, 0.029 mmol) and copper(I) iodide (2.78 mg, 0.015 mmol) were added and the mixture heated to 180° C. overnight. The reaction mixture was then cooled to RT and purified by normal phase chromatography, eluting with a gradient of 0-40% ethyl acetate in DCM and then further purified by MDAP (acidic conditions), to give the title compound (5 mg). LCMS (A) m/z: 470 [M+1]+, Rt 1.53 min (acidic).

Provenance & Evidence