A solution containing 2-(2-oxo-4-prop-2-ynyl-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (100 mg, 0.27 mmol), EXAMPLE 743, (3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester (87 mg, 0.27 mmol), EXAMPLE 69, Part B, Et3N (110 mg, 1.08 mmol), (Ph3P)4PdCl2 (10 mg, 0.013 mmol), and CuI (1 mg, 0.008 mmol) in anhydrous DMF (5 mL) is stirred at ambient temperature. After 5 h, the reaction mixture is diluted with EtOAc (50 mL) and water (50 mL) and the layers are separated. The aqueous layer is extracted twice with EtOAc (25 mL) and the combined organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue is purified by flash silica gel chromatography (CH2Cl2 to 10% MeOH CH2Cl2) to provide 77 mg (51%) of the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3, ˜2:1 mixture of rotamers) major rotamer: δ1.53 (s, 9H), 1.69 (s, 9H), 2.98 (m, 2H), 3.49 (s, 2H), 3.56 (m, 2H), 3.78 (s, 2H), 4.98 (s, 2H), 6.43 (s, 1H), 7.89 (m, 1H), 8.09 (m, 2H), 8.34 (m, 1H), 8.41 (m, 1H), 8.75 (m, 1H) ppm; MS (ISP loop): m/z 561 (M+H).
