Potassium Phosphate, Tribasic → HCID 71736587, compound

Participants

Reaction Steps

A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.023 g, 0.033 mmol), 4-(2-bromo-5-(trifluoromethyl)phenyl)morpholine (Intermediate G, 0.154 g, 0.497 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (Intermediate F, 0.140 g, 0.331 mmol), and potassium phosphate (0.281 g, 1.326 mmol) in 2.5 mL dioxane and 1 mL water was heated to 100° C. 2 hours. The reaction mixture was cooled to rt, diluted with EtOAc and washed with 1 N citric acid solution. The organic layers were dried over MgSO4 and concentrated. Purification of the resulting residue by reverse phase column chromatography [RediSep Gold C-18 50 g, 5 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 5-(2-morpholino-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.016 g, 0.030 mmol). [M+H]+=525.8 1H NMR (400 MHz, Acetone-d6) δ ppm: 8.23 (s, 1H), 7.38-7.44 (m, 1H), 7.26-7.36 (m, 3H), 7.14-7.22 (m, 2H), 4.35-4.40 (m, 2H), 3.39-3.49 (m, 3H), 3.28-3.38 (m, 2H), 2.86-2.96 (m, 2H), 2.73-2.81 (m, 2H), 2.47-2.60 (m, 1H)

Provenance & Evidence