[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([C:22]#[N:23])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.CC(O)=[O:26].Cl>CO.C(O[Pd]OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]3[C:12](=[C:11]([C:22]([NH2:23])=[O:26])[CH:10]=2)[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]3=2)[CH:6]=[CH:7][CH:8]=1To a 5 mL microwave vial 3′-methoxy-4-(pyridine-3-ylamino)biphenyl-3-carbonitrile (100.0 mg, 0.33 mmol), diacetoxypalladium (149.0 mg, 0.66 mmol) and AcOH (2 mL) were added. The vessel was sealed, and the reaction stirred at 160° C. 1 h. The reaction mixture was filtered and purified by preparative HPLC (100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B=80:20 and ending with A:B=0:100 [A=10% MeOH, 90% water, 0.1% TFA; B=90% MeOH, 10% water, 0.1% TFA] over 20 min). The HPLC fractions that contained the product were applied onto a cartridge of PHENOMENEX® Strata-X-C 33 um cation mixed-mode polymer. This was washed with methanol and the product was eluted with a 2N solution of ammonia in methanol. The solvents were removed and the product was converted to the HCl salt by adding a (1 eq) solution of 1N HCl in methanol. The solvents were removed to afford 12.00 mg of 8-(3-methoxyphenyl)-5H-pyrido[3,2-b]indole-6-carboxamide, carboxamide, HCl. MS (ESI) m/z 318.2 (M+H). 1H NMR (MeOD) d ppm 8.77-8.85 (3H, m), 8.62 (1H, d, J=1.83 Hz), 8.06 (1H, dd, J=8.24, 5.80 Hz), 7.48 (1H, t, J=7.93 Hz), 7.39-7.44 (2H, m), 7.04 (1H, dd, J=8.09, 1.68 Hz), 3.93 (3H, s).
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