Potassium Phosphate, Tribasic → HCID 89815597, compound

Participants

Reaction Steps

A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.023 g, 0.032 mmol), 1-methyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-1H-pyrazole (Intermediate O, 0.169 g, 0.481 mmol), 5-bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.120 g, 0.321 mmol), and potassium phosphate (0.272 g, 1.282 mmol) in 2.5 mL dioxane, 1.0 mL water was heated to 100° C. 4 hours. The reaction mixture was diluted with EtOAc and washed with 1 N citric acid solution. The organics were dried over MgSO4 and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.053 g, 0.102 mmol). [M+H]+=519.8 1H NMR (400 MHz, Acetone-d6) δ ppm: 7.88 (dd, J=8.0, 1.4 Hz, 1H), 7.81 (s, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.25 (d, J=2.0 Hz, 1H), 7.09-7.17 (m, 3H), 6.98-7.01 (m, 1H), 6.71 (d, J=4.7 Hz, 1H), 6.00 (d, J=2.0 Hz, 1H), 4.31 (d, J=15.7 Hz, 1H), 4.24 (d, J=15.7 Hz, 1H), 3.30-3.38 (m, 1H), 3.12 (m, 1H), 2.63-2.74 (m, 1H), 2.36-2.46 (m, 1H)

Provenance & Evidence