Reaction Steps
To a solution of 4-bromo-3-methyl-benzenesulfonyl chloride (120 mg, 0.37 mmol) in dioxane (5 ml) at room temperature, concentrated NH4OH (1 ml) was added. The mixture was stirred at room temperature for 4 h. A solution of the title compound from Example 21, Step A (100 mg, 0.14 mmol), sodium carbonate (30 mg, 0.28 mmol), and catalytic amount of tetrakis(triphenylphosphine) palladium (5% mol) in 14 ml of 1:2:4 mixture of water:EtOH:toluene was stirred under reflux for 6 h. The solvents were removed. Water (10 ml) was added. The mixture was extracted with methylene chloride (3×10 ml). The combined methylene chloride layers were washed with brine and dried over sodium sulfate. The title compound was obtained after reverse phase HPLC. 1H NMR (CDCl3, 500 MHz): δ a mixture of 1:1 atopoisomers 7.89 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.72 (s, 2H), 7.68 (m, 2H), 7.45 (t, J=8.0 Hz, 1H), 7.39 (m, 2H), 7.13 (m, 2H), 5.60 (d, J=8.5 Hz, 0.5H), 5.38 (d, J=8.5 Hz, 0.5H), 5.00 (d, J=16.0 Hz, 0.5H), 4.94 (d, J=16.0 Hz, 0.5H), 4.17 (d, J=16.0 Hz, 0.5H), 3.99 (d, J=16.0 Hz, 0.5H), 3.90 (s, 1.5H), 3.89 (s, 1.5H), 3.84 (m, 1H), 2.42 (s, 1.5H), 2.37 (s, 1.5), 1.75 (br s, 2H), 0.59 (d, J=6.5 Hz, 1.5H), 0.48 (d, J=7.0 Hz, 1.5H). LC/MS (M+1) 747.20.
